Name: 6882-68-4|(41S,7aR,13aR,13bR)-Dodecahydro-1H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10(41H)-one|96%
Brand: Ambeed
SKU: A102794
Price: 5.0 USD
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1
[ 6882-68-4 ]
[ 1345731-45-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydroxide; In water;Reflux;	<strong>[6882-68-4]Sophoridin</strong>e 1 (0.03 mol, 7.44 g) was dissolved in 2 N sodium hydroxide solution and heated toreflux for several days, after cooling down, the pH of the mixture was adjusted to 5-6 with 20% H2SO4and then filtered. The solution was evaporated under vacuum and the resultant solid was crystallizedin methanol, the yellow solid was obtained and dried under vacuum. Yield (85%), m.p. 154~155 C.C15H26N2O2 (266.4): MS(ESI) m/z: [M + H]+ = 267.2, [M - H] = 265.2.
		Compound 3 (5.0 g, 20.0 mmol)was added to 5 N NaOH (30 mL),which was refluxed for 9 h and then acidified with HCl (2 N) to pH6e7. The solvent was removed and the residue was refluxed for 2 hin methaol and MeOHwas removed to give 26, whichwas dissolvedwith CH2Cl2. Then substituted benzenesulfonyl chloride(20.0 mmol) and TEA (20 mmol) were added and stirred for 4 h,which was purified by flash column chromatography with CH2Cl2/CH3OH as the eluent to afford target compounds.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5251 - 5254
[2]Molecules,2018,vol. 23
[3]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 245 - 250
[4]Journal of Heterocyclic Chemistry,2019,vol. 56,p. 417 - 425
[5]European Journal of Medicinal Chemistry,2020,vol. 201
[6]ChemMedChem,2022,vol. 17

2
[ 6882-68-4 ]
(5R)-matrinic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.0%	With potassium hydroxide; In water; at 20℃; for 9h;Reflux;	12.4 g (0.05 mol) of <strong>[6882-68-4]sophoridine</strong> was provided, added to an aqueous solution of 33.6 g (0.6 mol, 12 eq.) of potassium hydroxide in 300 ml water, heated and refluxed for 9 h, then reacted at room temperature overnight. The reaction solution was cooled with ice-water bath and adjusted with 3N hydrochloric acid to PH5-6, concentrated in reduced pressure to dryness. The obtained solid was added to methanol and sufficiently dissolved, filtered, the filter cake was washed with methanol, the filtrates were combined and evaporated to dryness to obtained a crude product (5R)-matrinic acid. This yellow solid was recrystallized with ethanol/acetone to obtain a pure product (5R)-matrinic acid, total 12.1 g (yield: 91.0%). MS-ESI (M/Z): 267.1 [M+H]+ 1H NMR (CD3OD, 400 Hz, ppm): δ 3.54-3.50 (m, 1H), 3.44-3.37 (m, 1H), 3.30-3.23 (m, 3H), 3.21-3.15 (m, 1H), 3.06-3.02 (m, 1H), 2.95-2.92 (m, 1H), 2.84-2.78 (m, 1H), 2.47-2.39 (m, 1H), 2.27-2.23 (m, 2H), 2.17-2.14 (m, 1H), 2.01-1.55 (m, 10H), 1.36-1.25 (m, 1H).

Reference： [1]Patent: US2013/190345,2013,A1 .Location in patent: Paragraph 0564; 0565; 0566

3
[ 67-56-1 ]
[ 6882-68-4 ]
methyl sophoridinate dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Compound 1 (4.96g, 20mmol) was evenly dispersed in 6N hydrochloric acid solution (50ml) and heated to reflux for 4h. Then the solvent was evaporated under vacuum and anhydrous methanol (50ml) was added into the residue. The reaction mixture was stirred at room temperature for 2h, and then the solvent was evaporated under vacuum. The resultant solid was purified by flash chromatography over silica gel to obtain white solid 4 (6.72g, 95%). Mp 112-114C; 1H NMR (DMSO-d6) δ: 11.61 (s, 1H), 9.67 (s, 1H), 9.29 (s, 1H), 3.61 (s, 3H), 3.60-3.30 (m, 3H), 3.22-2.93 (m, 3H), 2.86-2.69 (m, 1H), 2.54-2.49 (m, 1H), 2.48-2.31 (m, 4H), 2.12 (m, 1H), 1.98-1.58 (m, 9H), 1.51-1.27 (m, 2H); 13C NMR δ: 172.8, 56.1, 55.4, 51.6, 51.3, 44.1, 41.6, 33.2, 32.8, 26.8, 24.9, 24.8, 21.8, 21.2, 20.8, 17.0; HRMS: calcd for C16H30N2O2Cl2 [M-2HCl+H]+, 281.2223; found, 281.2222.
	With hydrogenchloride; In water; for 24h;Reflux;	General procedure: To a solution of matrine (5.0 g, 20.1 mmol) in MeOH (50 mL) was added 2 mol/L hydrochloric acid(30 mL) and the reaction mixture was heated to reflux for 24 h. Then the solvent was evaporated undervacuum and the residue was triturated with acetone and filtered to aord compound 1 (5.4 g, 76%).

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 81,p. 95 - 105
[2]Molecules,2020,vol. 25

4
[ 60186-33-6 ]
[ 6882-68-4 ]
14-(4-(benzyloxy)-3-ethoxyphenylmethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium hydride; In tetrahydrofuran; mineral oil; at 37℃; for 13h;Reflux;	General procedure: Sophoridine(200 mg, 0.8 mmol) and 60% sodium hydride (806 mg, 20 mmol) into around-bottomed flask (50 mL) were resolved in anhydrous tetrahydrofuran (20mL). The solution was stirred and aldehyde (4 mmol) was added at 37 C andstirred for 1 h. The solution was then refluxed for 12 h. After cooling to roomtemperature, the mixture was pouredinto water (10 mL), acidified to pH=1~3 with 2N HCl and extracted with dichloromethane(3 × 40 mL). The aqueous phase was adjusted to pH=10~11 with 2N NaOH, and extracted with dichloromethane (3 × 40mL). The solvent was removed in vacuo, and the residue was purified by flashsilica gel column chromatography (petroleum ether/acetone, 10%) to afford 11-16.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1495 - 1497

5
[ 5533-06-2 ]
[ 6882-68-4 ]
14-(3-ethoxy-4-(methoxymethoxy)phenylmethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With sodium hydride; In tetrahydrofuran; mineral oil; at 37℃; for 13h;Reflux;	General procedure: <strong>[6882-68-4]Sophoridin</strong>e(200 mg, 0.8 mmol) and 60% sodium hydride (806 mg, 20 mmol) into around-bottomed flask (50 mL) were resolved in anhydrous tetrahydrofuran (20mL). The solution was stirred and aldehyde (4 mmol) was added at 37 C andstirred for 1 h. The solution was then refluxed for 12 h. After cooling to roomtemperature, the mixture was pouredinto water (10 mL), acidified to pH=1~3 with 2N HCl and extracted with dichloromethane(3 × 40 mL). The aqueous phase was adjusted to pH=10~11 with 2N NaOH, and extracted with dichloromethane (3 × 40mL). The solvent was removed in vacuo, and the residue was purified by flashsilica gel column chromatography (petroleum ether/acetone, 10%) to afford 11-16.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1495 - 1497

6
[ 120-57-0 ]
[ 6882-68-4 ]
14-(3,4-(methylenedioxy)phenylmethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With sodium hydride; In tetrahydrofuran; mineral oil; at 37℃; for 13h;Reflux;	General procedure: <strong>[6882-68-4]Sophoridin</strong>e(200 mg, 0.8 mmol) and 60% sodium hydride (806 mg, 20 mmol) into around-bottomed flask (50 mL) were resolved in anhydrous tetrahydrofuran (20mL). The solution was stirred and aldehyde (4 mmol) was added at 37 C andstirred for 1 h. The solution was then refluxed for 12 h. After cooling to roomtemperature, the mixture was pouredinto water (10 mL), acidified to pH=1~3 with 2N HCl and extracted with dichloromethane(3 × 40 mL). The aqueous phase was adjusted to pH=10~11 with 2N NaOH, and extracted with dichloromethane (3 × 40mL). The solvent was removed in vacuo, and the residue was purified by flashsilica gel column chromatography (petroleum ether/acetone, 10%) to afford 11-16.14-(3,4-(Methylenedioxy)phenylmethylene)<strong>[6882-68-4]sophoridine</strong>(11) (65 mg, 21%): 1H NMR(400 MHz, CDCl3): δ 7.67(1H, s), 6.80 (3H, m), 6.09 (2H, s), 3.59 (1H, dd, J = 5.2, 13.6 Hz), 3.49 (1H, m), 3.38 (1H, t, 12.8), 3.06 (1H, d, J = 11.2 Hz), 2.98 (1H, m), 2.83 (1H,m), 2.59 (1H, t, 12.8), 2.40-2.29 (4H, m), 2.12-1.16 (10H, m), 0.88 (1H, m). 13CNMR (100 MHz, CDCl3): δ165.0, 147.5, 147.3, 134.4, 129.8, 128.2, 124.2, 109.5, 108.2, 101.2, 62.1,55.4, 55.2, 49.6, 47.2, 39.3, 30.5, 29.0, 26.9, 23.4, 22.0, 21.1, 20.3.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1495 - 1497

7
[ 24973-22-6 ]
[ 6882-68-4 ]
14-(3-methoxy-4-methylphenylmethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With sodium hydride; In tetrahydrofuran; mineral oil; at 37℃; for 13h;Reflux;	General procedure: Sophoridine(200 mg, 0.8 mmol) and 60% sodium hydride (806 mg, 20 mmol) into around-bottomed flask (50 mL) were resolved in anhydrous tetrahydrofuran (20mL). The solution was stirred and aldehyde (4 mmol) was added at 37 C andstirred for 1 h. The solution was then refluxed for 12 h. After cooling to roomtemperature, the mixture was pouredinto water (10 mL), acidified to pH=1~3 with 2N HCl and extracted with dichloromethane(3 × 40 mL). The aqueous phase was adjusted to pH=10~11 with 2N NaOH, and extracted with dichloromethane (3 × 40mL). The solvent was removed in vacuo, and the residue was purified by flashsilica gel column chromatography (petroleum ether/acetone, 10%) to afford 11-16.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1495 - 1497

8
[ 52289-54-0 ]
[ 6882-68-4 ]
14-(4-methoxy-2-methylphenylmethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With sodium hydride; In tetrahydrofuran; mineral oil; at 37℃; for 13h;Reflux;	General procedure: <strong>[6882-68-4]Sophoridin</strong>e(200 mg, 0.8 mmol) and 60% sodium hydride (806 mg, 20 mmol) into around-bottomed flask (50 mL) were resolved in anhydrous tetrahydrofuran (20mL). The solution was stirred and aldehyde (4 mmol) was added at 37 C andstirred for 1 h. The solution was then refluxed for 12 h. After cooling to roomtemperature, the mixture was pouredinto water (10 mL), acidified to pH=1~3 with 2N HCl and extracted with dichloromethane(3 × 40 mL). The aqueous phase was adjusted to pH=10~11 with 2N NaOH, and extracted with dichloromethane (3 × 40mL). The solvent was removed in vacuo, and the residue was purified by flashsilica gel column chromatography (petroleum ether/acetone, 10%) to afford 11-16.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1495 - 1497

9
[ 6882-68-4 ]
[ 86-51-1 ]
14-(2,3-dimethoxyphenylmethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With sodium hydride; In tetrahydrofuran; mineral oil; at 37℃; for 13h;Reflux;	General procedure: <strong>[6882-68-4]Sophoridin</strong>e(200 mg, 0.8 mmol) and 60% sodium hydride (806 mg, 20 mmol) into around-bottomed flask (50 mL) were resolved in anhydrous tetrahydrofuran (20mL). The solution was stirred and aldehyde (4 mmol) was added at 37 C andstirred for 1 h. The solution was then refluxed for 12 h. After cooling to roomtemperature, the mixture was pouredinto water (10 mL), acidified to pH=1~3 with 2N HCl and extracted with dichloromethane(3 × 40 mL). The aqueous phase was adjusted to pH=10~11 with 2N NaOH, and extracted with dichloromethane (3 × 40mL). The solvent was removed in vacuo, and the residue was purified by flashsilica gel column chromatography (petroleum ether/acetone, 10%) to afford 11-16.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1495 - 1497

10
[ 6882-68-4 ]
[ 3392-97-0 ]
14-(2,5-dimethoxyphenylmethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With sodium hydride; In tetrahydrofuran; mineral oil; at 37℃; for 13h;Reflux;	General procedure: <strong>[6882-68-4]Sophoridin</strong>e(200 mg, 0.8 mmol) and 60% sodium hydride (806 mg, 20 mmol) into around-bottomed flask (50 mL) were resolved in anhydrous tetrahydrofuran (20mL). The solution was stirred and aldehyde (4 mmol) was added at 37 C andstirred for 1 h. The solution was then refluxed for 12 h. After cooling to roomtemperature, the mixture was pouredinto water (10 mL), acidified to pH=1~3 with 2N HCl and extracted with dichloromethane(3 × 40 mL). The aqueous phase was adjusted to pH=10~11 with 2N NaOH, and extracted with dichloromethane (3 × 40mL). The solvent was removed in vacuo, and the residue was purified by flashsilica gel column chromatography (petroleum ether/acetone, 10%) to afford 11-16.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1495 - 1497

11
[ 100-10-7 ]
[ 6882-68-4 ]
14-(4-(dimethylamino)phenylmethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With sodium hydride; In tetrahydrofuran; mineral oil; at 37℃; for 13h;Reflux;	General procedure: <strong>[6882-68-4]Sophoridin</strong>e(200 mg, 0.8 mmol) and 60% sodium hydride (806 mg, 20 mmol) into around-bottomed flask (50 mL) were resolved in anhydrous tetrahydrofuran (20mL). The solution was stirred and aldehyde (4 mmol) was added at 37 C andstirred for 1 h. The solution was then refluxed for 12 h. After cooling to roomtemperature, the mixture was pouredinto water (10 mL), acidified to pH=1~3 with 2N HCl and extracted with dichloromethane(3 × 40 mL). The aqueous phase was adjusted to pH=10~11 with 2N NaOH, and extracted with dichloromethane (3 × 40mL). The solvent was removed in vacuo, and the residue was purified by flashsilica gel column chromatography (petroleum ether/acetone, 10%) to afford 11-16.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1495 - 1497

12
[ 6882-68-4 ]
methyl 4-((1R,3aR,10aR,13aS)-decahydro-1H,4H-pyrido[3,2,1-ij][1,6]naphthyridin-1-yl)butyrate [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 245 - 250
[2]Patent: CN106928224,2017,A
[3]Molecules,2018,vol. 23
[4]European Journal of Medicinal Chemistry,2020,vol. 201
[5]ChemMedChem,2022,vol. 17

13
[ 6882-68-4 ]
C₁₅H₂₅N₂O₂^(1-)*K⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In water; at 120℃; for 10h;	To the 250 ml flask was added sequentially 10.0 g (40.3 mmol) of <strong>[6882-68-4]sophoridine</strong>, 30 g (0.54 mol) of potassium hydroxide and 100ml water, The mixture was stirred at 120 C for 10 h, After the end of the reaction, the mixture was cooled to room temperature, filtered and dried to give a white solid Potassium salt Π, without purification directly for the next step reaction;

Reference： [1]Patent: CN106928224,2017,A .Location in patent: Paragraph 0010

14
[ 67-56-1 ]
[ 6882-68-4 ]
methyl 4-((1R,3aR,10aR,13aS)-decahydro-1H,4H-pyrido[3,2,1-ij][1,6]naphthyridin-1-yl)butyrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of <strong>[6882-68-4]sophoridine</strong> (4.96 g, 20 mmol)Evenly dispersed in 50 mL6N HClIn an aqueous solution,Reflux reaction for 4 hours,TLC detection of raw materials disappeared,Stop the reaction,The solvent was evaporated to dryness under reduced pressure to give a yellow oil,Add 50 mL of anhydrous methanol,Stirred at room temperature for two hours,TLC detection reaction is complete,Vacuum drying solvent,A white solid,Using methylene chloride / methanol as the mobile phase,And purified by silica gel column chromatography.A white solid Z0A was obtained
		<strong>[6882-68-4]Sophoridin</strong>e 1 (2.48g, 10mmol) was hydrolyzed with 50mL of aqueous NaOH (2mol/L) under reflux for 8h, and then solvent was evaporated to get 2 in crude form. SOCl2 (3mL) was added to methanol (40mL) and stirred for 30min in ice-bath. Product 2 was then added portion-wise and the mixture was then refluxed for 3h. After completion of the reaction, the mixture was filtered and solvent was concentrated to obtain 3.

Reference： [1]Patent: CN107163047,2017,A .Location in patent: Paragraph 0107; 0109
[2]European Journal of Medicinal Chemistry,2018,vol. 156,p. 479 - 492

15
[ 110-62-3 ]
[ 6882-68-4 ]
C₂₀H₃₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h;	General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.
30%		Take a 100ml clean three-necked bottle and weigh 100mmol (2.4g) sodium hydride into a three-necked bottle. Connect the nitrogen protection device, set up the condensation return device, after nitrogen protection, measure and add 30ml of anhydrous tetrahydrofuran, set the temperature to 80C, start stirring and raise the temperature.Weigh 5mmol (1.24g) of <strong>[6882-68-4]sophoridine</strong>, dissolved in 10ml anhydrous tetrahydrofuran, slowly added to the reaction system, until the temperature rose to 80 C, reaction 30min.When there are no more bubbles in the system, 4 equivalents, namely 20 mmol of valeraldehyde, are added slowly and the reaction is refluxed for 8 hours. During the reaction, the reaction is monitored by thin layers and the reaction is determined to be completed. Post-reaction treatment: After the reaction is completed, the temperature is lowered to room temperature, after which a 1 mol/L hydrochloric acid solution is prepared, the pH of the reaction solution is adjusted to 7-8, and a small amount of chloroform is used to extract the reaction solution.Take the organic phase, after the extraction is complete, combine the organic phase, add an appropriate amount of anhydrous sodium sulfate to remove water, and let stand overnight.After that, the solvent was distilled off under reduced pressure and purified on a silica gel column.The eluent was eluted with a dichloromethane-methanol system with a gradient elution. The product spot was separated from a dichloromethane:methanol ratio of 20:1 to 40:3.

Reference： [1]Molecules,2017,vol. 22
[2]Patent: CN107629053,2018,A .Location in patent: Paragraph 0028; 0030; 0031; 0032; 0035

16
[ 100-52-7 ]
[ 6882-68-4 ]
C₂₂H₂₈N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h;	General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.

Reference： [1]Molecules,2017,vol. 22

17
[ 123-11-5 ]
[ 6882-68-4 ]
14-(4-methoxybenzylidene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h;	General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.

Reference： [1]Molecules,2017,vol. 22

18
[ 104-88-1 ]
[ 6882-68-4 ]
14-(4-chlorobenzylidene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h;	General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.

Reference： [1]Molecules,2017,vol. 22

19
[ 939-97-9 ]
[ 6882-68-4 ]
C₂₆H₃₆N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h;	General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.

Reference： [1]Molecules,2017,vol. 22

20
[ 66-99-9 ]
[ 6882-68-4 ]
C₂₆H₃₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h;	General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.

Reference： [1]Molecules,2017,vol. 22

21
[ 98-01-1 ]
[ 6882-68-4 ]
C₂₀H₂₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h;	General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.

Reference： [1]Molecules,2017,vol. 22

22
[ 98-03-3 ]
[ 6882-68-4 ]
C₂₀H₂₆N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h;	General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.

Reference： [1]Molecules,2017,vol. 22

23
[ 7283-96-7 ]
[ 6882-68-4 ]
C₂₀H₂₅ClN₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h;	General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containingsophoridine (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35?40 °C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5percent, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a?2k.

Reference： [1]Molecules,2017,vol. 22

24
[ 13679-70-4 ]
[ 6882-68-4 ]
C₂₁H₂₈N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h;	General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.

Reference： [1]Molecules,2017,vol. 22

25
[ 5834-16-2 ]
[ 6882-68-4 ]
C₂₁H₂₈N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h;	General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containingsophoridine (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.

Reference： [1]Molecules,2017,vol. 22

26
[ 74-96-4 ]
[ 6882-68-4 ]
14-ethylsophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%		General procedure: To a round-bottomed flask (100 mL) containing LDA (3 mL) and <strong>[6882-68-4]sophoridine</strong> (5 mmol, 1.24 g)dissolved in anhydrous tetrahydrofuran (50 mL) was added dropwise at 0 C and stirred for 40 min,then alkyl halide (0.02 mol) was added and reacted at room temperature for 5 h. The mixturewas treated with hydrochloric acid (5%, 20 mL) to neutralize and then extracted with chloroform(3 x 20 mL). The combined organic layer was dried with anhydrous sodium sulfate and thenconcentrated. The residue was purified by silica gel column chromatography using CH3COOEt/CHCl3(50:1, v/v) as eluent to give the compounds 3a-3f.
40%		Take a clean 100ml three-necked flask and attach a nitrogen protection device. Measure 3 ml of LDA into a three-necked flask and start stirring in an ice bath.Weigh 5mmol (1.24g) <strong>[6882-68-4]sophoridine</strong> dissolved in 40ml anhydrous tetrahydrofuran, slowly added dropwise to the reaction system, stirring 40min.Weigh 4 times the equivalent of 20mmol of ethyl bromide, slowly added to the reaction system, stirred at room temperature for 5h.During the reaction, the reaction was monitored in real time using thin-layer chromatography to confirm the end of the reaction. Post-reaction treatment: 50 ml of saturated sodium bicarbonate solution was added to the reaction system to quench the reaction, and the reaction was terminated. After stirring for 30 minutes,A small amount of chloroform was used for extraction several times and the organic phase was taken. After the extraction was complete, the organic phases were combined.Take an appropriate amount of anhydrous sodium sulfate to dry the water, and seal the plastic wrap overnight.The dried extract was distilled under reduced pressure to remove the solvent and purified on a silica gel column. The eluent was eluted with an ethyl acetate-chloroform system. The product was eluted with a gradient of ethyl acetate:chloroform of 50:1.

Reference： [1]Molecules,2017,vol. 22
[2]Patent: CN107629053,2018,A .Location in patent: Paragraph 0058; 0060; 0061; 0062; 0065

27
[ 109-65-9 ]
[ 6882-68-4 ]
14-butylsophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		General procedure: To a round-bottomed flask (100 mL) containing LDA (3 mL) and <strong>[6882-68-4]sophoridine</strong> (5 mmol, 1.24 g)dissolved in anhydrous tetrahydrofuran (50 mL) was added dropwise at 0 C and stirred for 40 min,then alkyl halide (0.02 mol) was added and reacted at room temperature for 5 h. The mixturewas treated with hydrochloric acid (5%, 20 mL) to neutralize and then extracted with chloroform(3 x 20 mL). The combined organic layer was dried with anhydrous sodium sulfate and thenconcentrated. The residue was purified by silica gel column chromatography using CH3COOEt/CHCl3(50:1, v/v) as eluent to give the compounds 3a-3f.

Reference： [1]Molecules,2017,vol. 22

28
[ 111-25-1 ]
[ 6882-68-4 ]
14-hexylsophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%		General procedure: To a round-bottomed flask (100 mL) containing LDA (3 mL) and <strong>[6882-68-4]sophoridine</strong> (5 mmol, 1.24 g)dissolved in anhydrous tetrahydrofuran (50 mL) was added dropwise at 0 C and stirred for 40 min,then alkyl halide (0.02 mol) was added and reacted at room temperature for 5 h. The mixturewas treated with hydrochloric acid (5%, 20 mL) to neutralize and then extracted with chloroform(3 x 20 mL). The combined organic layer was dried with anhydrous sodium sulfate and thenconcentrated. The residue was purified by silica gel column chromatography using CH3COOEt/CHCl3(50:1, v/v) as eluent to give the compounds 3a-3f.

Reference： [1]Molecules,2017,vol. 22

29
[ 100-39-0 ]
[ 6882-68-4 ]
14-benzylsophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%		General procedure: To a round-bottomed flask (100 mL) containing LDA (3 mL) and <strong>[6882-68-4]sophoridine</strong> (5 mmol, 1.24 g)dissolved in anhydrous tetrahydrofuran (50 mL) was added dropwise at 0 C and stirred for 40 min,then alkyl halide (0.02 mol) was added and reacted at room temperature for 5 h. The mixturewas treated with hydrochloric acid (5%, 20 mL) to neutralize and then extracted with chloroform(3 x 20 mL). The combined organic layer was dried with anhydrous sodium sulfate and thenconcentrated. The residue was purified by silica gel column chromatography using CH3COOEt/CHCl3(50:1, v/v) as eluent to give the compounds 3a-3f.

Reference： [1]Molecules,2017,vol. 22

30
[ 4437-18-7 ]
[ 6882-68-4 ]
C₂₀H₂₈N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%		General procedure: To a round-bottomed flask (100 mL) containing LDA (3 mL) and <strong>[6882-68-4]sophoridine</strong> (5 mmol, 1.24 g)dissolved in anhydrous tetrahydrofuran (50 mL) was added dropwise at 0 C and stirred for 40 min,then alkyl halide (0.02 mol) was added and reacted at room temperature for 5 h. The mixturewas treated with hydrochloric acid (5%, 20 mL) to neutralize and then extracted with chloroform(3 x 20 mL). The combined organic layer was dried with anhydrous sodium sulfate and thenconcentrated. The residue was purified by silica gel column chromatography using CH3COOEt/CHCl3(50:1, v/v) as eluent to give the compounds 3a-3f.

Reference： [1]Molecules,2017,vol. 22

31
[ 45438-73-1 ]
[ 6882-68-4 ]
C₂₀H₂₈N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		General procedure: To a round-bottomed flask (100 mL) containing LDA (3 mL) and <strong>[6882-68-4]sophoridine</strong> (5 mmol, 1.24 g)dissolved in anhydrous tetrahydrofuran (50 mL) was added dropwise at 0 C and stirred for 40 min,then alkyl halide (0.02 mol) was added and reacted at room temperature for 5 h. The mixturewas treated with hydrochloric acid (5%, 20 mL) to neutralize and then extracted with chloroform(3 x 20 mL). The combined organic layer was dried with anhydrous sodium sulfate and thenconcentrated. The residue was purified by silica gel column chromatography using CH3COOEt/CHCl3(50:1, v/v) as eluent to give the compounds 3a-3f.

Reference： [1]Molecules,2017,vol. 22

32
[ 6882-68-4 ]
C₁₅H₂₆N₂O₂*2ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; for 8h;Reflux;	Take <strong>[6882-68-4]sophoridine</strong> 4.96g (0.02mol), add 100ml hydrochloric acid (6mol / L), heated to reflux 8h,Concentrated under reduced pressure and evaporated to dryness, and then 100 ml of methanol was added. The mixture was stirred at room temperature for 6 hours and evaporated to dryness under reduced pressure to give crude <strong>[6882-68-4]sophoridine</strong>.The white solid with dichloromethane / methanol as the mobile phase, separated and purified by silica gel column,A white product was obtained (5.20 g, 92%) which was identified as HDZ-0A in the test. HDZ-0A is<strong>[6882-68-4]Sophoridin</strong>e methyl ester.

Reference： [1]Patent: CN104250247,2016,B .Location in patent: Paragraph 0119; 0120

33
[ 6882-68-4 ]
C₁₅H₂₃ClN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In dichloromethane; at 20℃; for 2.5h;Reflux;	General procedure: <strong>[6882-68-4]Sophoridin</strong>e 1, (2 eq., 10 mmol) POCl3 (2.48 g, 5 mmol) were firstly dissolved in DCM (30 mL). The mixture was stirred at room temperature until its colour changed to yellow, and was then refluxed for 2.5 h. Aromatic ammonia (1-1.5 eq.) dissolved in DCM was added drop-wise to the solution and refluxed for 12 h. After completion of the reaction,NaOH or NaHCO3 aqueous was added to neutralize and then extracted with chloroform (3×20 mL). The combined organic layer was dried with anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography using DCM/EA (3:1-1:1,v/v) as eluent to give the compounds 3a-3o.

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 4136 - 4144

34
[ 23842-82-2 ]
[ 6882-68-4 ]
4-amino-6-methoxyquinolinosophoridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 4136 - 4144

35
[ 23842-82-2 ]
[ 6882-68-4 ]
C₂₃H₃₀N₄O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 4136 - 4144

36
[ 6526-08-5 ]
[ 6882-68-4 ]
C₂₃H₂₇F₃N₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 4136 - 4144

37
[ 1192-58-1 ]
[ 6882-68-4 ]
14-(N-methylpyrrol-2-ylmethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.
23%	With sodium hydride; In tetrahydrofuran; at 85℃; for 36h;	2.4 g (100 mmol) of sodium hydride and 50 mL of anhydrous tetrahydrofuran were added to a 100 mL round bottom flask.Stir well, add 1.24 g (5 mmol) of <strong>[6882-68-4]sophoridine</strong>, slowly warm to 85 C, add 0.654 g (6 mmol) of N-methyl-2-pyrrolidine, and react for 36 h to the end point (TLC detection).After cooling to room temperature, excess sodium hydride was neutralized by dropwise addition of 3N hydrochloric acid.Dichloromethane extraction (40 mL×3), the organic phase was combined, dried over anhydrous Na2SO4.(V dichloromethane: V methanol = 50:1) was purified to give 0.389 g of light brown solid powder LYL-01: 14-(N-methyl-2-pyrrol-2-ylmethylene)<strong>[6882-68-4]sophoridine</strong>: yield 23%;

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682
[2]Patent: CN108358923,2018,A .Location in patent: Paragraph 0033; 0034; 0035; 0036; 0037; 0038; 0039

38
[ 18159-24-5 ]
[ 6882-68-4 ]
14-(N-benzylpyrrol-2-ylmethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

39
[ 946774-66-9 ]
[ 6882-68-4 ]
14-[N-(2-methylbenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

40
[ 946687-14-5 ]
[ 6882-68-4 ]
14-[N-(3-methylbenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

41
[ 6882-68-4 ]
[ 946774-42-1 ]
14-[N-(4-methylbenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

42
[ 1482541-99-0 ]
[ 6882-68-4 ]
14-[N-(3,5-dimethylbenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

43
C₁₆H₁₉NO [ No CAS ]
[ 6882-68-4 ]
14-[N-(4-tert-butylbenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

44
C₂₀H₂₇NO [ No CAS ]
[ 6882-68-4 ]
14-[N-(3,5-di-tert-butylbenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

45
[ 6882-68-4 ]
[ 883541-16-0 ]
14-[N-(4-fluorobenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

46
[ 946700-45-4 ]
[ 6882-68-4 ]
14-[N-(2-chlorobenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

47
1-(3-chlorobenzyl)-1H-pyrrole-2-carbaldehyde [ No CAS ]
[ 6882-68-4 ]
14-[N-(3-chlorobenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

48
[ 6882-68-4 ]
[ 159636-80-3 ]
14-[N-(4-chlorobenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

49
[ 156210-54-7 ]
[ 6882-68-4 ]
14-[N-(2-bromobenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

50
1-(4-bromobenzyl)pyrrole-2-carbaldehyde [ No CAS ]
[ 6882-68-4 ]
14-[N-(4-bromobenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

51
1-(3-methoxybenzyl)-1H-pyrrole-2-carbaldehyde [ No CAS ]
[ 6882-68-4 ]
14-[N-(3-methoxybenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

52
[ 6882-68-4 ]
[ 861162-64-3 ]
14-(1-(4-methoxybenzyl)-2-pyrrolemethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

53
C₁₄H₁₅NO₃ [ No CAS ]
[ 6882-68-4 ]
14-[N-(3,5-dimethoxybenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

54
C₁₃H₁₂BrNO₂ [ No CAS ]
[ 6882-68-4 ]
14-[N-(2-bromo-5-methoxybenzyl)pyrrol-2-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

55
C₁₆H₁₃NO [ No CAS ]
[ 6882-68-4 ]
14-(1-(β-naphthalenylmethyl)-2-pyrrolemethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

56
C₁₉H₁₇NO₂ [ No CAS ]
[ 6882-68-4 ]
14-(1-(4-(phenylmethoxy)benzyl)-2-pyrrolemethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

57
C₁₃H₁₀F₃NO₂ [ No CAS ]
[ 6882-68-4 ]
14-(1-(4-trifluoromethoxybenzyl)-2-pyrrolemethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%		A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and 50mL anhydrous tetrahydrofuran. The solution was stirred at room temperature for 1h and then N-substituted pyrrole-2-carboxyaldehyde 2 (2a-2u) (5mmol) was added followed by reflux for 48h. Reaction mixture was cooled and poured into water slowly (100mL). Reaction mixture was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 1%) to afford 3a-3u in 23%-54% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

58
[ 10511-51-0 ]
[ 6882-68-4 ]
14-[N-benzyl-1H-indol-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.
51%	With sodium hydride; In tetrahydrofuran; at 85℃; for 48h;	2.4 g (100 mmol) of sodium hydride and 50 mL of anhydrous tetrahydrofuran were added to a 100 mL round bottom flask.Stir well, add 1.24 g (5 mmol) of <strong>[6882-68-4]sophoridine</strong>, slowly warm to 85 C, add 1.41 g (6 mmol) of N-benzyl-3-indolaldehyde, and react for 48 h to the end point (TLC detection).After cooling to room temperature, excess sodium hydride was neutralized by dropwise addition of 3N hydrochloric acid.Dichloromethane extraction (40 mL×3), the organic phase was combined, dried over anhydrous Na2SO4.(V Dichloromethane: V methanol = 50:1) was purified to give 1.185 g of a white solid powder as a base compound LMY-22: 14-[N-benzylindolin-3-ylmethylene]<strong>[6882-68-4]sophoridine</strong> The yield is 51%;

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682
[2]Patent: CN108358923,2018,A .Location in patent: Paragraph 0033; 0082; 0084; 0085; 0086; 0087

59
[ 428495-34-5 ]
[ 6882-68-4 ]
14-[N-(2-methylbenzyl)-1H-indo-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

60
[ 428470-09-1 ]
[ 6882-68-4 ]
14-[N-(3-methylbenzyl)-1H-indo-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

61
[ 151409-79-9 ]
[ 6882-68-4 ]
14-[N-(4-methylbenzyl)-1H-indo-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

62
C₁₈H₁₇NO [ No CAS ]
[ 6882-68-4 ]
14-[N-(3,5-dimethylbenzyl)-1H-indo-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

63
1-(4-tert-butylbenzyl)indole-3-carboxaldehyde [ No CAS ]
[ 6882-68-4 ]
14-[N-(4-tert-butylbenzyl)-1H-indo-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

64
[ 90815-00-2 ]
[ 6882-68-4 ]
14-[N-(2-chlorobenzyl)-1H-indo-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

65
[ 75629-57-1 ]
[ 6882-68-4 ]
14-[N-(4-chlorobenzyl)-1H-indo-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

66
[ 93548-80-2 ]
[ 6882-68-4 ]
14-[N-(2,6-dichlorobenzyl)-1H-indo-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

67
[ 171734-73-9 ]
[ 6882-68-4 ]
14-[N-(2-bromobenzyl)-1H-indo-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

68
[ 174367-69-2 ]
[ 6882-68-4 ]
14-[N-(3-bromobenzyl)-1H-indo-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

69
[ 174367-70-5 ]
[ 6882-68-4 ]
14-[N-(4-bromobenzyl)-1H-indo-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

70
[ 6882-68-4 ]
N-(3-methoxybenzyl)-indole-3-carboxaldehyde [ No CAS ]
14-[N-(3-methoxybenzyl)-1H-indol-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

71
[ 928835-08-9 ]
[ 6882-68-4 ]
14-[N-(4-methoxybenzyl)-1H-indol-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

72
C₁₈H₁₇NO₃ [ No CAS ]
[ 6882-68-4 ]
14-[N-(3,5-dimethoxybenzyl)-1H-indol-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

73
C₁₇H₁₄BrNO₂ [ No CAS ]
[ 6882-68-4 ]
14-[N-(2-bromo-5-methoxybenzyl)-1H-indol-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

74
C₂₀H₁₅NO [ No CAS ]
[ 6882-68-4 ]
14-(1-(β-naphthalenylmethyl)-3-indolemethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

75
1-(4-benzyloxybenzyl)indole-3-carbaldehyde [ No CAS ]
[ 6882-68-4 ]
14-(1-(4-(phenylmethoxy)benzyl)-3-indolemethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

76
C₁₇H₁₂F₃NO₂ [ No CAS ]
[ 6882-68-4 ]
14-[N-(4-trifluoromethoxybenzyl)-1H-indol-3-methylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

77
C₂₄H₂₁NO₂ [ No CAS ]
[ 6882-68-4 ]
14-(1-(4-(phenylmethoxy)benzyl)-5-methy-3-indolemethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

78
C₂₃H₁₈ClNO₂ [ No CAS ]
[ 6882-68-4 ]
14-(1-(4-(phenylmethoxy)benzyl)-6-chloro-3-indolemethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

79
C₂₃H₁₈BrNO₂ [ No CAS ]
[ 6882-68-4 ]
14-(1-(4-(phenylmethoxy)benzyl)-5-bromo-3-indolemethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

80
C₂₄H₂₁NO₃ [ No CAS ]
[ 6882-68-4 ]
14-(1-(4-(phenylmethoxy)benzyl)-5-methoxy-3-indolemethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

81
[ 192996-80-8 ]
[ 6882-68-4 ]
14-(1-(4-(phenylmethoxy)benzyl)-4-indolemethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

82
C₂₃H₁₉NO₂ [ No CAS ]
[ 6882-68-4 ]
14-(1-(4-(phenylmethoxy)benzyl)-5-indolemethylene)sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

83
C₂₄H₂₁NO₂ [ No CAS ]
[ 6882-68-4 ]
14-[N-(4-(4-methylbenzyloxy)benzyl)-1H-indol-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%		General procedure: A 100mL round-bottom flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by the addition of N-substituted indole-carboxyaldehyde 9 (9a-9l) (5mmol) and then refluxed for 48h. The mixture was cooled and poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 10a-10l in 29%-59% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

84
C₂₅H₂₃NO₃ [ No CAS ]
[ 6882-68-4 ]
14-[5-methoxy-N-(4-(4-methylbenzyloxy)benzyl)-1H-indol-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		General procedure: A 100mL round-bottom flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by the addition of N-substituted indole-carboxyaldehyde 9 (9a-9l) (5mmol) and then refluxed for 48h. The mixture was cooled and poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 10a-10l in 29%-59% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

85
C₂₇H₂₇NO₂ [ No CAS ]
[ 6882-68-4 ]
14-[N-(4-(4-tert-butylbenzyloxy)benzyl)-1H-indol-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		General procedure: A 100mL round-bottom flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by the addition of N-substituted indole-carboxyaldehyde 9 (9a-9l) (5mmol) and then refluxed for 48h. The mixture was cooled and poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 10a-10l in 29%-59% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

86
C₂₈H₂₉NO₃ [ No CAS ]
[ 6882-68-4 ]
14-[5-methoxy-N-(4-(4-tert-butylbenzyloxy)benzyl)-1H-indol-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%		General procedure: A 100mL round-bottom flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by the addition of N-substituted indole-carboxyaldehyde 9 (9a-9l) (5mmol) and then refluxed for 48h. The mixture was cooled and poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 10a-10l in 29%-59% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

87
C₂₃H₁₈FNO₂ [ No CAS ]
[ 6882-68-4 ]
14-[N-(4-(4-fluorobenzyloxy)benzyl)-1H-indol-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%		General procedure: A 100mL round-bottom flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by the addition of N-substituted indole-carboxyaldehyde 9 (9a-9l) (5mmol) and then refluxed for 48h. The mixture was cooled and poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 10a-10l in 29%-59% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

88
C₂₄H₂₀FNO₃ [ No CAS ]
[ 6882-68-4 ]
14-[5-methoxy-N-(4-(4-fluorobenzyloxy)benzyl)-1H-indol-3-ylmethylene]sophoridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		General procedure: A 100mL round-bottom flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by the addition of N-substituted indole-carboxyaldehyde 9 (9a-9l) (5mmol) and then refluxed for 48h. The mixture was cooled and poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The organic phase was dried with anhydrous Na2SO4 and concentrated to give crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 10a-10l in 29%-59% yields.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 665 - 682

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	6882-68-4	MDL No. :	MFCD00238686
Formula :	C₁₅H₂₄N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZSBXGIUJOOQZMP-BHPKHCPMSA-N
M.W :	248.36	Pubchem ID :	165549
Synonyms :	Sophoradin;5-Epidihydrosophocarpine;(-)-Sophoridine;Dihydro-5-episophocarpine	Chemical Name :	(41S,7aR,13aR,13bR)-Dodecahydro-1H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10(41H)-one

Num. heavy atoms :	18
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.93
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	79.58
TPSA :	23.55 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.69 cm/s

[ CAS No. 6882-68-4 ] {[proInfo.proName]}

Quality Control of [ 6882-68-4 ]

Related Doc. of [ 6882-68-4 ]

Product Details of [ 6882-68-4 ]

Calculated chemistry of [ 6882-68-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6882-68-4 ]

Application In Synthesis of [ 6882-68-4 ]

[ 6882-68-4 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 6882-68-4 ]

Amides

Related Parent Nucleus of
[ 6882-68-4 ]

Other Aliphatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	2.7
Log Po/w (XLOGP3) :	1.58
Log Po/w (WLOGP) :	1.11
Log Po/w (MLOGP) :	2.27
Log Po/w (SILICOS-IT) :	1.34
Consensus Log Po/w :	1.8

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.38
Solubility :	1.05 mg/ml ; 0.00421 mol/l
Class :	Soluble
Log S (Ali) :	-1.69
Solubility :	5.13 mg/ml ; 0.0206 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.68
Solubility :	5.17 mg/ml ; 0.0208 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.2

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P501-P270-P264-P301+P310+P330-P405	UN#:	1544
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 6882-68-4 ] {[proInfo.proName]}

Quality Control of [ 6882-68-4 ]

Related Doc. of [ 6882-68-4 ]

Product Details of [ 6882-68-4 ]

Calculated chemistry of [ 6882-68-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6882-68-4 ]

Application In Synthesis of [ 6882-68-4 ]

[ 6882-68-4 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 6882-68-4 ]

Amides

Related Parent Nucleus of [ 6882-68-4 ]

Other Aliphatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 6882-68-4 ]

Related Parent Nucleus of
[ 6882-68-4 ]