[ CAS No. 364794-80-9 ] {[proInfo.proName]}

Name: 364794-80-9|4-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine|97%
Brand: Ambeed
SKU: A109836
Price: 23.0 USD
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Quality Control of [ 364794-80-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 364794-80-9 ]

Product Details of [ 364794-80-9 ]

CAS No. :	364794-80-9	MDL No. :	MFCD06797489
Formula :	C₁₇H₂₆BNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RCGRLLZELIIKDH-UHFFFAOYSA-N
M.W :	303.20	Pubchem ID :	2795578
Synonyms :

Calculated chemistry of [ 364794-80-9 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.65
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	92.89
TPSA :	30.93 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.37
Log Po/w (WLOGP) :	1.29
Log Po/w (MLOGP) :	1.3
Log Po/w (SILICOS-IT) :	2.19
Consensus Log Po/w :	1.43

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.22
Solubility :	0.184 mg/ml ; 0.000607 mol/l
Class :	Soluble
Log S (Ali) :	-2.66
Solubility :	0.663 mg/ml ; 0.00219 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.58
Solubility :	0.00807 mg/ml ; 0.0000266 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.17

Safety of [ 364794-80-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 364794-80-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 364794-80-9 ]
Downstream synthetic route of [ 364794-80-9 ]

[ 364794-80-9 ] Synthesis Path-Upstream 1~9

1
[ 73183-34-3 ]
[ 364793-86-2 ]
[ 364794-79-6 ]
[ 364794-80-9 ]

Reference： [1] Patent: US2002/26052, 2002, A1,

2
[ 110-91-8 ]
[ 443776-76-9 ]
[ 364794-80-9 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853

3
[ 110-91-8 ]
[ 214360-74-4 ]
[ 364794-80-9 ]

Reference： [1] ACS Combinatorial Science, 2011, vol. 13, # 1, p. 24 - 31

4
[ 73183-34-3 ]
[ 364793-82-8 ]
[ 364794-80-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2989 - 2992
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 2, p. 196 - 218
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3820 - 3832

5
[ 73183-34-3 ]
[ 364793-82-8 ]
[ 364794-80-9 ]

Reference： [1] Patent: US2002/26052, 2002, A1,

6
[ 73183-34-3 ]
[ 364793-86-2 ]
[ 364794-79-6 ]
[ 364794-80-9 ]

Reference： [1] Patent: US2002/26052, 2002, A1,

7
[ 76-09-5 ]
[ 364794-80-9 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853

8
[ 87199-15-3 ]
[ 364794-80-9 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853

9
[ 3132-99-8 ]
[ 364794-80-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2989 - 2992

[ 364794-80-9 ] Synthesis Path-Downstream 1~35

1
[ 73183-34-3 ]
[ 364793-82-8 ]
[ 364794-80-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 179,p. 449 - 469
[2]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2989 - 2992
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 196 - 218
[4]Journal of Medicinal Chemistry,2013,vol. 56,p. 3820 - 3832

2
[ 364794-80-9 ]
[ 364793-60-2 ]
4-(2,4-Dichloro-5-methoxyanilino)-7-[3-(4-morpholinylmethyl)-phenyl]-3-quinolinecarbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2989 - 2992

3
[ 364794-80-9 ]
[ 364793-73-7 ]
4-(2,4-Dichloro-5-methoxyanilino)-6-methoxy-7-[3-(4-morpholinylmethyl]phenyl }-3-quinolinecarbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2989 - 2992

4
[ 956034-15-4 ]
[ 364794-80-9 ]
C₂₁H₂₃ClN₄O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; at 100℃; for 0.166667 - 0.666667h;Microwave irradiation;	Example 223 2-(lH-indazol-4-yl)-4-morpholino-6-(3-(morpholinomethyl)phenyl)thieno[3,2-d]pyrimidine 299[00823] 2-Chloro-6-iodo-4-morpholinothieno[3,2-£/lpyrimidine 19 (50 mg) was <n="215"/>coupled to 4-[3-(4,4,5,5-tetramethyl-l,332-dioxaborolan-2-yl)]benzylmorpholine, and then reacted with 4-(4,4,5,5-tetramemyl-l,3,2-dioxaborolan-2-yl)-17Wndazole 7 via GeneralProcedure F. The product was purified by reverse phase HPLC to yield 2.6 mg of 299. MS.(Ql) 513.2 (M)+; General Procedure F Suzuki coupling reactions in one pot[00245] 2-CMoro-64odo-4rmorpholmothieno[3,2-£?]pyrimidine 19 (leq), phenylboronic acid or heterocycleboronic acid (R1 -B(OH)2, 1.1 eq) and bis(triphenylphosphine)palladium(II) dichloride (O.leq) in lMNa2CC>3 aqueous solution (3 eq) and acetonitrile (3eq) was heated to 100 0C in a sealed microwave reactor for 10 to 40 min to give 20. Upon completion, 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH- indazole 7 (1.3 eq) and bis(triphenylphosphine)palladium(II) dichloride (O.leq) were added in the same pot. The reaction mixture was heated to 150 0C in a sealed microwave reactor for 10 to 15min. The mixture was extracted with ethyl acetate (3 x 5 mL). The combined organic layers were concentrated to yield crude 21.

Reference： [1]Patent: WO2007/127183,2007,A1 .Location in patent: Page/Page column 131; 213-214

5
[ 3132-99-8 ]
[ 364794-80-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2989 - 2992

6
[ 73183-34-3 ]
[ 364793-82-8 ]
4-(2,4-Dichloro-5-methoxyanilino)-7-[3-(4-morholinylmethyl) phenyll-3-quinolinecarbonitrile [ No CAS ]
[ 364794-80-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate; In water; dimethyl sulfoxide; ethyl acetate; toluene;	EXAMPLE 26 4-(2,4-Dichloro-5-methoxyanilino)-7-[3-(4-morholinylmethyl) phenyll-3-quinolinecarbonitrile To a dry flask under a nitrogen atmosphere was added 200 mg (0.78 mmol) of 4-(3-bromobenzyl) morpholine, 0.218 g (0.86 mmol) of bis(pinacolato) diboron, 230 mg (2.34 mmol) of potassium acetate, 5 mL of dimethylsulfoxide and 32 mg (0.04 mmol) of [1,1'-bis(diphenylphosphino) ferrocene]dichloropalladium(II), complex with dichloromethane. The reaction mixture was heated at 80 C. for 2 hours. After cooling, the mixture was partitioned between 20 mL of toluene, 40 mL of ethyl acetate and 40 mL of water. The layers were separated and the aqueous layer was further extracted with 30 mL of ethyl acetate. The organic layers were combined and washed with 4*40 mL water. After drying over magnesium sulfate, removal of the solvents gave crude 4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzyl]morpholine as a dark oil.

Reference： [1]Patent: US2002/26052,2002,A1

7
[ 73183-34-3 ]
[ 364793-86-2 ]
[ 364794-79-6 ]
[ 364794-80-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate; In dichloromethane; dimethyl sulfoxide;	EXAMPLE 28 4-(2,4-Dichloro-5-methoxyanilino)-7-3-[2-(4-morpholinvl) ethvllphenyl }-3-quinolinecarbonitrile By the procedure used to prepare 4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzyl]morpholine, in Example 26, 1.0 g (3.70 mmol) of <strong>[364793-86-2]4-(3-bromophenethyl) morpholine</strong>, was reacted with 1.03 g (4.07 mmol) of bis(pinacolato) diboron, 1.1 g (11.0 mmol) of potassium acetate and 0.3 g (0.37 mmol) of [1,1'-bis(diphenylphosphino) ferrocene]dichloropalladium(II), complex with dichloromethane in 25 mL of anhydrous dimethylsulfoxide to provide crude 4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenethyllmorpholine. This material was purified by flash silica gel chromatography, eluding with a gradient of 99:1 methylene chloride/methanol to 97.5:2.5 methylene chloride/methanol, to provide 0.52 g of 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzyl]morpholine as a light brown liquid; MS (ES) m/z 318.3 (M+1).

Reference： [1]Patent: US2002/26052,2002,A1

8
[ 747413-06-5 ]
[ 364794-80-9 ]
C₃₇H₃₆ClN₃O₅ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 196 - 218

9
[ 1161498-11-8 ]
[ 364794-80-9 ]
[ 1161500-58-8 ]

Yield	Reaction Conditions	Operation in experiment
		Example 109: (S)-N-((S)-l-Cyano-2-(3'-(morpholinomethyl)biphenyl-4- yl)ethyl)piperidine-2-carboxamide ditrifluoroacetate(S)-tert-Buty{ 2-((S)- 1 -cyano-2-(4-iodophenyl)ethylcarbamoyl)piperidine- 1 -carboxylate (200 mg) and 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (2.70 mg) in dioxane (5 mL) were treated with 4-(3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzyl)morpholine (188 mg) and the mixture was stirred at room temperature for 15 min under nitrogen. An aqueous solution of potassium carbonate (2M, 0.414 mL) was added and the mixture was stirred for 18 h at 75 0C. After 4 further additions of 1,1 bis(di-tert- butylphosphino)ferrocene palladium dichloride the mixture was heated for a total of 48 h. The mixture was evaporated and ethyl acetate was added. The resulting dark brown mixture was purified by flash silica chromatography, eluting with 20% ethyl acetate in isohexane and then with 40% ethyl acetate in isohexane containing 0.5% triethylamine to give a colourless oil. Formic acid (2 mL) was added and the mixture was heated at 50 0C for 12 min. The cooled mixture was basified with 0.880 aqueous ammonia and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulphate, filtered and the solvent was evaporated. The resulting oil was purified by preparative HPLC on a Waters X-Bridge column using a 95-5% gradient of aqueous 0.1% TFA in acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford the title compound (0.054g) as a yellow oil.1H NMR (399.825 MHz, D2O) delta 7.82 (d, J = 7.9 Hz, IH), 7.77 (s, IH), 7.73 - 7.68 (m, 2H), 7.62 (t, J = 7.8 Hz, IH), 7.52 (d, J = 7.7 Hz, IH), 7.49 - 7.43 (m, 2H), 5.08 (t, J = 7.8 Hz, <n="156"/>IH), 4.45 (s, 2H), 4.11 (d, J = 12.3 Hz, 2H), 3.90 - 3.83 (m, IH), 3.79 (t, J = 12.3 Hz, 2H), 3.48 (d, J = 12.3 Hz, 3H), 3.43 - 3.18 (m, 4H), 3.02 (t, J = 21.7 Hz, IH), 2.16 - 2.04 (m, IH), 1.99 - 1.82 (m, 2H), 1.80 - 1.44 (m, 3H) m/z 433 [M+H]+

Reference： [1]Patent: WO2009/74829,2009,A1 .Location in patent: Page/Page column 154-155

10
[ 1062295-41-3 ]
[ 364794-80-9 ]
N-{(2S)-5-[3-(4-morpholinylmethyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; for 16h;Inert atmosphere; Reflux;	Example 7: N-{(2S)-5-[3-(4-morpholinylmethyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2- propanesulfonamideA mixture of N-[(2S)-5-bromo-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (100 mg, 0.31 mmol, Description 1 ), 4-[3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenyl]methyl}morpholine (114 mg, 0.38 mmol), Pd(PPh3)4 (3.6 mg, 3.1 umol), and Na2CO3 (67 mg, 0.63 mmol) in a 3:1 mixture of dioxane:water (2 ml) was stirred and refluxed at 90 0C under argon for 16 hours. The mixture was allowed to cool and was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic solution was dried (MgSO4) and evaporated under reduced pressure to yield the crude product as a yellow oil, which was purified using MDAP. The resulting material was partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane. The organic solution was dried (MgSO4) and evaporated under reduced pressure to yield the desired product as a white foam (81 mg, 62%). LC/MS (ES): Found 415 (ES+), retention time 0.74 mins (2 minute run). C23H30N2O3S requires 414.1H NMR (400MHz, CDCI3): delta 7.51-7.53 (1 H, m), 7.41-7.47 (3H, m), 7.38 (1 H, t, J = 7 Hz), 7.27-7.32 (2H, m), 4.28-4.39 (2H, m), 3.70-3.74 (4H, m), 3.56 (2H, s), 3.33-3.42 (2H, m), 3.21 (1 H, septet, J = 7 Hz), 2.92-3.01 (2H, m), 2.46-2.50 (4H, m), 1.41 (6H, d, J = 7 Hz).

Reference： [1]Patent: WO2010/66658,2010,A1 .Location in patent: Page/Page column 28; 29

11
[ 110-91-8 ]
[ 214360-74-4 ]
[ 364794-80-9 ]

Reference： [1]ACS Combinatorial Science,2011,vol. 13,p. 24 - 31

12
[ 99-90-1 ]
[ 364794-80-9 ]
[ 1177195-80-0 ]

Reference： [1]ACS Combinatorial Science,2011,vol. 13,p. 24 - 31

13
[ 1049093-75-5 ]
[ 364794-80-9 ]
[ 1382722-81-7 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5797 - 5812

14
[ 851684-46-3 ]
[ 364794-80-9 ]
[ 1432450-84-4 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3820 - 3832

15
[ 1338796-33-0 ]
[ 364794-80-9 ]
[ 1430464-38-2 ]

Yield	Reaction Conditions	Operation in experiment
27%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 125℃; for 0.5h;Inert atmosphere; Microwave irradiation;	To a mixture of N-(3-iodo-lH-indazol-5-yl)-2-(pyrrolidin-l-yl)-2- (thiophen-3-yl)acetamide (56.6 mg, 0.125 mmol) and 4-(3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)benzyl)morpholine (33.3 mg, 0.11 mmol) in PhCH3/EtOH (1.5 mL/3 mL) was added 1 M aq Na2C03 (0.3 mL, 0.3 mmol), followed by Pd(PPh3)4 (5.8 mg, 0.005 mmol). The resulting mixture was purged with Ar and microwaved 30 min at 125 C. After removal of solvents, it was purified by flash chromatography (EtO Ac/hex 0 to 100 %, then MeOH/DCM 5-15 %) and then triturated with Et20 to give the title compound as beige solid (15 mg, 27 %). ? NMR (400 MHz, CD3OD) delta 8.37 (s, 1H), 7.91 (s, 1H), 7.83 (d, J = 6.8 Hz, 1H), 7.55-7.47 (m, 4H), 7.45-7.39 (m, 2H), 7.35 (d, J = 4.8 Hz, 1H), 4.15 (s, 1H), 3.72 (t, J = 4.6 Hz, 4H), 3.65 (s, 2H), 2.75-2.65 (m, 2H), 2.60-2.50 (m, 6H), 1.90-1.85 (m, 4H); MS ESI 502.2 [M + H]+, calcd for [C28H31N502S + H]+ 502.2.

Reference： [1]Patent: WO2013/53051,2013,A1 .Location in patent: Page/Page column 157

16
[ 1443284-06-7 ]
[ 364794-80-9 ]
[ 1443283-80-4 ]

Yield	Reaction Conditions	Operation in experiment
0.106 g	With tetrakis(triphenylphosphine) palladium(0); tripotassium phosphate dihydrate; In 1,2-dimethoxyethane; water; at 150℃; for 0.25h;Inert atmosphere; Microwave irradiation;	To 149 mg (0.48 mmol) of 6-chloro-1 -methyl-3-(3-pyridyl)-4-(trifluoromethyl)-1 H- pyrazolo[3,4-b]pyridine in 4.8 ml of a 1/1 DME/H20 mixture under an inert atmosphere of argon are added 0.173 g (0.57 mmol) of 4-[3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)benzyl]morpholine, 0.355 g (1.43 mmol) of potassium phosphate dihydrate and 1 1 mg (0.01 mmol) of tetrakis(triphenylphosphine)palladium. The reaction medium is heated at 150C for 15 minutes by microwave. The reaction medium is hydrolysed with water and then extracted with dichloromethane. The organic phase is dried over sodium sulfate and then concentrated under reduced pressure. The residue obtained is purified by column chromatography on silica gel, eluting with a dichloromethane/methanol mixture. After recrystallization from diisopropyl ether, 0.106 g of a white solid is obtained. MH+: 454 Melting point: 155C 1H NMR (400 MHz, DMSO-d6) delta 8.68 - 8.74 (m, 2 H), 8.22 - 8.29 (m, 2 H), 8.19 (s, 1 H), 7.96 (dt, J=7.9 Hz, 1 .7 Hz, 1 H), 7.50 - 7.61 (m, 3 H), 4.28 (s, 3 H), 3.55 - 3.69 (m, 6 H), 2.43 (m, 4 H)

Reference： [1]Patent: WO2013/87744,2013,A1 .Location in patent: Page/Page column 38-39

17
[ 110-91-8 ]
[ 443776-76-9 ]
[ 364794-80-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4850 - 4853

18
[ 76-09-5 ]
[ 364794-80-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4850 - 4853

19
[ 87199-15-3 ]
[ 364794-80-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4850 - 4853

20
tert-butyl 6-bromo-3-formylimidazo[1,2-a]pyrazine-8-yl(cyclopropyl)carbamate [ No CAS ]
[ 364794-80-9 ]
tert-butyl cyclopropyl(3-formyl-6-(3-(morpholinomethyl)phenyl)imidazo[1,2-a]pyrazin-8-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; for 2h;Reflux;	Example 182 Synthesis of tert-butyl cyclopropyl(3-formyl-6-(3-(morpholinomethyl)phenyl)imidazo[1,2-a]pyrazin-8-yl)carbamate Tert-butyl 6-bromo-3-formylimidazo[1,2-a]pyrazine-8-yl(cyclopropyl)carbamate (100 mg, 0.26 mmol), <strong>[364794-80-9]4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]morpholine</strong> (118 mg, 0.39 mmol), 3M Na2CO3 (1.3 mL, 2.60 mmol) and DME (3.5 mL) were combined. The solution was degassed with a stream of N2 for 10 min. Pd(PPh3)4 was added and the solution was refluxed for 2 h. The solution was partitioned between dichloromethane (25 mL) and water (25 mL). The aqueous layer was further extracted with dichloromethane (2*25 mL). The organics were washed with brine (50 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified via preparative TLC (5% MeOH/dichloromethane) to afford tert-butyl cyclopropyl(3-formyl-6-(3-(morpholinomethyl)phenyl)imidazo[1,2-a]pyrazin-8-yl)carbamate (60 mg, 48%). LCMS (ES): >95% pure, m/z 478 [M+1]+.
48%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; for 2h;Inert atmosphere; Reflux;	Tert-butyl 6-bromo-3-formylimidazo[1,2-a]pyrazine-8-yl(cyclopropyl)carbamate (100 mg, 0.26 mmol), <strong>[364794-80-9]4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]morpholine</strong> (118 mg, 0.39 mmol), 3M Na 2CO 3 (1.3 mL, 2.60 mmol) and DME (3.5 mL) were combined. The solution was degassed with a stream of N 2 for 10 min. Pd(PPh 3) 4 was added and the solution was refluxed for 2 h. The solution was partitioned between dichloromethane (25 mL) and water (25 mL). The aqueous layer was further extracted with dichloromethane (2×25 mL). The organics were washed with brine (50 mL), dried over MgSO 4, filtered and concentrated in vacuo. The residue was purified via preparative TLC (5% MeOH/dichloromethane) to afford tert-butyl cyclopropyl(3-formyl-6-(3-(morpholinomethyl)phenyl)imidazo[1,2-a]pyrazin-8-yl)carbamate (60 mg, 48%).

Reference： [1]Patent: US9303033,2016,B2 .Location in patent: Page/Page column 276
[2]Patent: JP5802676,2015,B2 .Location in patent: Paragraph 0528

21
7-bromo-5-(1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine [ No CAS ]
[ 364794-80-9 ]
7-(3-(morpholinomethyl)phenyl)-5-(1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4256 - 4260

22
7-bromo-5-(1-cyclohexyl-1H-pyrazol-5-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine [ No CAS ]
[ 364794-80-9 ]
5-(1-cyclohexyl-1H-pyrazol-5-yl)-7-(3-(morpholinomethyl)phenyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4256 - 4260

23
1-(4-chloro-5-fluoro-2-nitrophenyl)-4-methylpiperazine [ No CAS ]
[ 364794-80-9 ]
4-((2'-fluoro-4‘-(4-methylpiperazin-1-yl)-5‘-nitro-[1,1'-biphenyl]-3-yl)methyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54.7%	With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); sodium carbonate; XPhos; In 1,4-dioxane; water; at 90℃;Inert atmosphere; Sealed tube;	A vial was charged with the mixture obtained in l-(4-chloro-5-fluoro-2-nitrophenyl)-4-methylpiperazine,<strong>[364794-80-9]3-(4-morpholinomethyl)phenylboronic acid pinacol ester</strong> (0.498 g, 1.642 mmol), XPhos Pd G2 (0.017 g, 0.022 mmol), and XPhos (10.44 mg, 0.022 mmol). The vial was sealed with a cap and septum, evacuated and backfilled with nitrogen. 1,4-Dioxane (volume: 10 ml) and a 2M aq. solution of sodium carbonate monohydrate (ACS) (2.74 ml, 5.47 mmol) were added via syringe and the vial was evacuated and backfilled with nitrogen an additional time. The reaction was heated at 90C in an aluminum block overnight. LCMS indicated complete consumption of the starting material(s). The peak at 1.56 minutes ionized for the mass of the target product. The reaction was cooled to room temperature and concentrated onto celite. Purification by silica gel flash chromatography [1 -10% MeOH/DCM + l% NH4OH;] afforded the desired4-((2'-fluoro-4'-(4-methylpiperazin- l-yl)-5'-nitro-[l,Gamma-biphenyl]-3-yl)methyl)mo holine (0.248 g, 0.598 mmol, 54.7% yield) as a yellow oil. LCMS [M+H]+ 415 g/mol.

Reference： [1]Patent: WO2017/147700,2017,A1 .Location in patent: Paragraph 00198

24
1-(4-bromo-5-fluoro-2-nitrophenyl)-N,N-dimethylpyrrolidin-3-amine [ No CAS ]
[ 364794-80-9 ]
1-(2-fluoro-3‘-(morpholinomethyl)-5-nitro-[1,1‘-biphenyl]-4-yl)-N,N-dimethylpyrrolidin-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); sodium carbonate; XPhos; In 1,4-dioxane; water; at 95℃;Inert atmosphere; Sealed tube;	A vial was charged with a mixture of l-(4-bromo-5-fluoro-2- nitrophenyl)-N,N-dimethylpyrrolidin-3-amine (0.092 g, 0.28 mmol, prepared as described in Example 21 above), <strong>[364794-80-9]3-(4-morpholinomethyl)phenylboronic acid pinacol ester</strong> (0.12 g, 0.39 mmol), XPhos Pd G2 (0.0044 g, 0.005 mmol) and XPhos (0.0026 g, 0.005 mmol). The vial was sealed with a septum cap and evacuated and backfilled with nitrogen. 1,4-Dioxane (4 mL) and 2M Aq sodium carbonate (0.70 mL, 1.4 mmol) were added via syringe. The vial was evacuated and backfilled an additional time before being heated at 95 C overnight. The reaction was cooled to room temperature and concentrated directly onto celite. Flash chromatography [0.5-10% MeOH/DCM + 1% NH4OH] afforded 1 -(2-fluoro-3'-(morpholinomethyl)-5 -nitro-[1 , 1 '-biphenyl] -4-yl)-N,N- dimethylpyrrolidin-3-amine (0.110 g, 86 %). LCMS [M+H]+: 429.5.

Reference： [1]Patent: WO2017/147700,2017,A1 .Location in patent: Paragraph 00290

25
4-(4-chloro-5-fluoro-2-nitrophenyl)-1,2-dimethylpiperazine [ No CAS ]
[ 364794-80-9 ]
4-((4‘-(3,4-dimethylpiperazin-1-yl)-2‘-fluoro-5‘-nitro-[1,1‘-biphenyl]-3-yl)methyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); sodium carbonate; XPhos; In 1,4-dioxane; water; at 100℃;Inert atmosphere;	A vial was charged with the mixture obtained in Step 1 (0.22 g), 3-(4- mo holinomethyl) henylboronic acid pinacol ester (0.16 g, 0.52 mmol), XPhos Pd G2 (0.006 g, 0.007 mmol) and XPhos (0.004 g, 0.007 mmol). The vial was sealed with a septum cap and evacuated and backfilled with nitrogen. 1,4-Dioxane (4 mL) and a 2M aq. solution of sodium carbonate (0.90 mL, 1.7 mmol) were added via syringe. The vial was evacuated and backfilled an additional time before being heated at 100 C in an aluminum block overnight. The reaction was cooled to room temperature and concentrated directly onto celite. Flash chromatography [0.5-5% MeOH/DCM + 1% NH4OH] afforded the desired 4-((4'-(3,4-dimethylpiperazin-1-yl)-2'-fluoro-5'-nitro- [1,Gamma-MurhoEtabetaetagamma1]-3-gamma1^betaiotagamma1)piiotaomicronphiEtaomicron1etabeta (0.18 g, 62%). LCMS [M+H]+: 429.7.

Reference： [1]Patent: WO2017/147700,2017,A1 .Location in patent: Paragraph 00277

26
(R)-4-(4-chloro-5-fluoro-2-nitrophenyl)-1,2-dimethylpiperazine [ No CAS ]
[ 364794-80-9 ]
(R)-4-((4‘-(3,4-dimethylpiperazin-1-yl)-2‘-fluoro-5‘-nitro-[1,1'-biphenyl]-3-yl)methyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); sodium carbonate; XPhos; In 1,4-dioxane; water; at 100℃;Inert atmosphere;	A 30 mL vial was charged with a mixture of (R)-4-(4-chloro-5-fluoro-2- nitrophenyl)-l,2-dimethylpiperazine (0.050 g, 0.174 mmol), 3-(4- mophiholinomethyl)phenylboronic acid pinacol ester (0.074 g, 0.243 mmol), XPhos Pd G2 (2.73 mg, 3.48 muetaiotaomicron) and XPhos (1.657 mg, 3.48 muetaiotaomicron). The vial was sealed with a cap/septum, evacuated and backfilled with nitrogen. 1,4-Dioxane (2 ml) and 2M Aq sodium carbonate (0.434 ml, 0.869 mmol) were added via syringe and the vial was evacuated and backfilled an additional time. The reaction was heated in an aluminum block overnight at 100 C. LCMS indicated very clean conversion to the desired product. The reaction mixture was loaded onto celite and purified by flash chromatography [0.1-5% MeOH/DCM + 1% NH4OH] to afford the product (0.152 mmol, 87 % yield) as a yellow film.

Reference： [1]Patent: WO2017/147700,2017,A1 .Location in patent: Paragraph 00285

27
[ 364794-80-9 ]
6-chloro-N-[4-(4-methylpiperazin-1-yl)-3'-morpholin-4-ylmethyl-biphenyl-3-yl]-4-trifluoromethylnicotinamide [ No CAS ]

Reference： [1]Chem,2018,vol. 4,p. 522 - 532

28
[ 364794-80-9 ]
6-oxo-4-trifluoromethyl-1,6-dihydro-pyridine-3-carboxylic acid [4-(4-methyl-piperazin-1-yl)-3'-morpholin-4-ylmethyl-biphenyl-3-yl]-amide [ No CAS ]

Reference： [1]Chem,2018,vol. 4,p. 522 - 532

29
5-bromo-2-(4-methyl-piperazin-1-yl)-phenylamine [ No CAS ]
[ 364794-80-9 ]
4-(4-methyl-piperazin-1-yl)-3'-morpholin-4-ylmethyl-biphenyl-3-ylamine trihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%		A stirring solution of <strong>[364794-80-9]4-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-morpholine</strong> 22 (5.37 g,17.7 mmol), 5-bromo-2-(4-methyl-piperazin-1-yl)-phenylamine 24 (3.97 g, 14.7 mmol), potassiumphosphate (9.43 g, 44.4 mmol), water (4.12 mL) and 1-butanol (68.0 mL) in a 250 mL round bottomsealed tube pressure vessel was purged with nitrogen, then SPhos Pd G2 (0.750 g, 1.04 mmol) wasadded in one portion, the mixture was purged for an additional 5 min, then the mixture was sealedand heated at 70 C in an oil bath overnight. The crude reaction mixture was allowed to cool to roomtemperature, was filtered through celite with warm 95% EtOH:H2O (3 x 50 mL) and concentrated toafford a brown solid. The crude solid was diluted with EtOH (200 mL), cooled to 0 C in an ice bathand concentrated HCl (20 mL) was added in one portion. The mixture was removed from the ice bathand stirred for 1h at room temperature. The resulting suspension was filtered, washed with cold EtOH(2 x 50 mL) and dried under vacuum to afford 6.85 g (98%) of 4-(4-methyl-piperazin-1-yl)-3'-morpholin-4-ylmethyl-biphenyl-3-ylamine hydrochloride 26. 1H NMR (400 MHz, DMSO-d6) delta 7.97 (s,1H), 7.72 - 7.60 (m, 4H), 7.59 - 7.51 (m, 1H), 7.38 (d, J = 8.3 Hz, 1H), 4.44 (s, 2H), 3.95 - 3.79 (m,4H), 3.49 (d, J = 11.5 Hz, 2H), 3.42 - 3.08 (m, 11H), 2.82 (s, 3H). 13C NMR (400 MHz, DMSO-d6) delta143.12, 139.45, 136.94, 131.22, 130.83, 130.11, 130.01, 129.53, 127.55, 125.13, 122.75, 120.57,63.05, 58.78, 52.64, 50.63, 48.37, 42.15. LRMS m/z calcd. for C22H30N4O ([M+H]+) 367.25, found367.46.

Reference： [1]Chem,2018,vol. 4,p. 522 - 532

30
(R)-3-bromo-6-((4-hydroxy-1-(3-phenylbutanoyl)piperidin-4-yl)methyl)-2-methyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one [ No CAS ]
[ 364794-80-9 ]
(R)-6-((4-hydroxy-1-(3-phenylbutanoyl)piperidin-4-yl)methyl)-2-methyl-3-(3-(morpholinomethyl)phenyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 238 - 243

31
[ 956034-15-4 ]
[ 364794-80-9 ]
2-(1H-indazol-4-yl)-4-morpholino-6-(3-(morpholinomethyl)phenyl)thieno[3,2-d]pyrimidine [ No CAS ]

Reference： [1]Patent: WO2007/127183,2007,A1

32
[ 1403993-19-0 ]
[ 364794-80-9 ]
(R)-4-(3-(5-(1-(quinuclidin-3-yl)-1H-1,2,3-triazol-4-yl)thiophen-2-yl)benzyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 150℃; for 0.25h;Inert atmosphere; Microwave irradiation; Sealed tube;	General procedure: To a mixture of derivative of type IV (50 mg, 0.147 mmol) intoluene (1.5 mL) and EtOH (0.75 mL) were successively added thedesired boronic ester or acid of type V (0.176 mmol, 1.2 eq.), K2CO3(0.294 mmol, 2.0 eq.) and Pd(PPh3)4 (0.0147 mmol, 10 mol %). Thereaction mixture was degassed with Ar and irradiated under microwavefor 20 min at 150 C. Alternatively PdCl2(dppf) 10 mol %,could be used as catalyst. In this case the base was switched toNa2CO3 (2.0 eq.) and the irradiation performed for 40 min at 100 C.In both cases, after cooling, the volatiles were removed underreduced pressure and the crude material purified by flash chromatography(CH2Cl2/MeOH 80/20 NH4OH 0.1 mL).

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 179,p. 449 - 469

33
[ 823-78-9 ]
[ 364794-80-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 179,p. 449 - 469

34
[ 1404051-38-2 ]
[ 364794-80-9 ]
(R)-4-((3'-(1-(quinuclidin-3-yl)-1H-1,2,3-triazol-4-yl)[1,1′-biphenyl]-3-yl)methyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 150℃; for 0.25h;Inert atmosphere; Microwave irradiation; Sealed tube;	General procedure: To a mixture of derivative of type IV (50 mg, 0.147 mmol) intoluene (1.5 mL) and EtOH (0.75 mL) were successively added thedesired boronic ester or acid of type V (0.176 mmol, 1.2 eq.), K2CO3(0.294 mmol, 2.0 eq.) and Pd(PPh3)4 (0.0147 mmol, 10 mol %). Thereaction mixture was degassed with Ar and irradiated under microwavefor 20 min at 150 C. Alternatively PdCl2(dppf) 10 mol %,could be used as catalyst. In this case the base was switched toNa2CO3 (2.0 eq.) and the irradiation performed for 40 min at 100 C.In both cases, after cooling, the volatiles were removed underreduced pressure and the crude material purified by flash chromatography(CH2Cl2/MeOH 80/20 NH4OH 0.1 mL).

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 179,p. 449 - 469

35
[ 364794-80-9 ]
[ 87476-73-1 ]

Reference： [1]Tetrahedron Letters,2020,vol. 61

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 364794-80-9 ] {[proInfo.proName]}

Quality Control of [ 364794-80-9 ]

Related Doc. of [ 364794-80-9 ]

Product Details of [ 364794-80-9 ]

Calculated chemistry of [ 364794-80-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 364794-80-9 ]

Application In Synthesis of [ 364794-80-9 ]

[ 364794-80-9 ] Synthesis Path-Upstream 1~9

[ 364794-80-9 ] Synthesis Path-Downstream 1~35

Related Functional Groups of [ 364794-80-9 ]

Organoboron

Aryls

Related Parent Nucleus of [ 364794-80-9 ]

Aliphatic Heterocycles

Morpholines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 364794-80-9 ]

Related Parent Nucleus of
[ 364794-80-9 ]