56622-54-9|(6-Methylpyridin-3-yl)methanamine| Ambeed

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Quality Control of [ 56622-54-9 ] Purity: 95% SDS Specification

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Product Details of [ 56622-54-9 ]

CAS No. :	56622-54-9
Formula :	C₇H₁₀N₂
M.W :	122.17
SMILES Code :	CC1=CC=C(CN)C=N1
MDL No. :	MFCD06212657
InChI Key :	NZPFQOXRHLUPRT-UHFFFAOYSA-N
Pubchem ID :	12214337

Safety of [ 56622-54-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H315-H318-H335
Precautionary Statements:	P280-P301+P310+P330-P302+P352-P305+P351+P338+P310
Class:	6.1
UN#:	2810
Packing Group:	Ⅲ

Application In Synthesis of [ 56622-54-9 ]

* 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.

Downstream synthetic route of [ 56622-54-9 ]

[ 56622-54-9 ] Synthesis Path-Downstream 1~35

1
[ 3222-48-8 ]
[ 56622-54-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With ammonia; hydrogen; In methanol; at 20℃; for 2h;	Procedure H: To a mixture of 6-methylnicotinonitrile (300 mg, 2.54 mmol) in MeOH/NH3 (7N, 10mL), was added Raney Ni (50 mg). The reaction mixture was stirred at RT for 3 h under H2. It was then filtered, and the filtrate concentrated in vacuo to give 6- methylpyridin-3-yl) methanamine as a yellow oil (280 mg, 90%). LC-MS (ESI): m/z (M+1)+ = 123.30.
	With ammonia; hydrogen;nickel; In methanol; at 20℃; under 3102.97 Torr; for 3h;	6-Methyl-nicotinonitrile (80 mg, 0.7 mmol) and Raney Ni (60 mg, prewashed with methanol) was mixed in 30 mL of ammonia (20% solution in methanol). The heavy walled reaction vessel was charged with H2 (60 psi) and the reaction was shaken at room temperature for 3 h. The mixture was filtered to remove the catalyst, and the filtrate was concentrated to afford an oil (50 mg). This oil was dissolved in 2 mL of anhydrous N,N-dimethylformamide, followed by the addition of 4-amino-5-cyano-6-ethoxy-pyridine-2-carboxylic acid (52 mg, 0.25 mmol), O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate (94 mg, 0.3 mmol), and N,N-diisopropylamine (52 muL, 0.3 mmol). The mixture was stirred at room temperature for 20 h. The crude product was purified via reverse phase HPLC (0-70% CH3CN in 10 mM aq. TFA) to provide 35 mg (45%) of the titled compound as the TFA salt. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.33 (t, J=7.1 Hz, 3H), 2.63 (s, 3H), 4.45-4.60 (m, 4H), 7.05 (s, 1H), 7.34 (bs, 2H), 7.71 (d, J=8.1 Hz, 1H), 8.18 (d, J=8.1 Hz, 1H), 8.64 (s, 1H), 9.18 (t, J=6.3 Hz, 1H). MS (ESI+) m/e=312 (M+H)+.
	With ammonia; hydrogen; In methanol; at 40℃; under 2585.81 Torr; for 12h;Inert atmosphere;	To a solution of 6-methylpyridine-3-carbonitrile (10.5 g, 25.7 mmol) in MeOH (80 mL) and NHs/MeOH (20 mL, 7 M) was added Raney-Ni (2.0 g) under N2 atmosphere. The suspension was degassed in vacuo and refilled with H2. The mixture was stirred for 12 hrs at 40 C under H2 (50 psi) atmosphere. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give (6-methyl-3-pyridyl)methylamine (9.5 g, compound 34b) as a light oil. 1H NMR (400 MHz, DMSO- d6) delta ppm: 8.36 (s, 1H), 7.62 (d, 7 = 8.0 Hz, 1H), 7.18 (d, / = 8.0 Hz, 1H), 3.69 (s, 2H), 2.42 (s, 3H). MS obsd. (ESI+) [(M+H)+]: 123.

References: [1]Patent: WO2019/213570,2019,A1 .Location in patent: Paragraph 0331; 0402-0404.
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 2586 - 2593.
[3]Journal fur praktische Chemie (Leipzig 1954),1936,vol. <2> 146,p. 88,102.
[4]Patent: US2006/173050,2006,A1 .Location in patent: Page/Page column 74.
[5]Patent: WO2016/180695,2016,A1 .Location in patent: Page/Page column 126; 127.
[6]Journal of Medicinal Chemistry,2017,vol. 60,p. 7965 - 7983.

2
[ 56622-54-9 ]
[ 34107-46-5 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1936,vol. <2> 146,p. 88,102.
[2]Journal fur praktische Chemie (Leipzig 1954),1936,vol. <2> 146,p. 88,102.

3
[ 56622-54-9 ]
6-methyl-pyridine-3-carbaldehyde-phenylhydrazone [ No CAS ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1936,vol. <2> 146,p. 88,102.

4
[ 28900-10-9 ]
[ 56622-54-9 ]

References: [1]Journal of the American Chemical Society,1947,vol. 69,p. 2574,2577.

5
[ 56622-54-9 ]
[ 108-24-7 ]
N-(6-Methyl-pyridin-3-ylmethyl)-acetamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2586 - 2593.

Yield	Reaction Conditions	Operation in experiment
	With palladium 10% on activated carbon; hydrogen; at 20℃; for 3h;	General procedure: b) pyridin-2-ylmethanamine 10% Palladium charcoal (0.05 g) was added to a stirred solution of 2-(azidomethyl) pyridine as obtained in step a) (0.22 g, 0.002 moles) at room temperature. The reaction mixture was stirred under hydrogen atmosphere for 3 h. Once the starting material was consumed (monitored by TLC), the reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure. The crude product was obtained as gummy solid (0.12 g) which was used in the next step without further purification. 1 H NMR (400 MHz, DMSO): delta 8.54 (t, J = 6.6 Hz; 1 H), 7.82-7.76 (m, 1 H), 1.52-1 Al (m, 1 H), 7.31 -7.24 (m, 1 H), 4.1 1-4.06 (m, 1 H), 3.88 (br s, 1 H), 3.84 (m, 1 H); MS (ES-MS): m/z 109.1 (M + 1 ).

7
[ 56622-54-9 ]
[ 183742-23-6 ]
[ 874446-71-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 507 - 511.

8
[ 56622-54-9 ]
[ 959756-38-8 ]

Yield	Reaction Conditions	Operation in experiment
		Step 1 2-Methoxy-N-(6-methylpyriotan-3-yl)methyl-4-mtrobenzamiotade[00365] 2-Methoxy-4-mtrobenzoic acid (293 mg, 1 49 mmol) is dissolved m DMF (2 mL) and 4- methylmorpholme (220 muL, 3 0 mmol) and TBTU (1 79 g, 1 7 mmol) are added The mixture is stirred at rt for 30 mm and C-(6-methylpy?dm-3-yl)methylamme (400 mg, 3 27 mmol) is added Stirring is continued at rt for 12 h DCM (10 mL) is added and the organic phase is washed with Na2CC"3 (5% aq ), HCl (3% aq ) and water, and then dried over Na2SO4 After evaporation of the solvents, the residue is triturated with ether-hexane to afford the title compound as a white solid
		2-Methoxy-4-nitrobenzoic acid (293 mg, 1.49 mmol) is dissolved in DMF (2 mL) and4-methylmorpholine (220 muL, 3.0 mmol) and TBTU (1.79 g, 1.7 mmol) are added. The mixture is stirred at rt for 30 min and <strong>[56622-54-9]C-<strong>[56622-54-9](6-methylpyridin-3-yl)methylamine</strong></strong> (400 mg, 3.27 mmol) is added. Stirring is continued at rt for 12 h. DCM (10 mL) is added and the organic phase is washed with Na2CO3 (5% aq.), HCl (3% aq.) and water, and then dried over Na2SOzI. After evaporation of the solvents, the residue is triturated with ether-hexane to afford the title compound as a white solid.

References: [1]Patent: WO2007/131991,2007,A1 .Location in patent: Page/Page column 94.
[2]Patent: WO2007/138072,2007,A2 .Location in patent: Page/Page column 108.

9
[ 56622-54-9 ]
3-[(6-methyl-pyridin-3-ylmethyl)-carbamoyl]-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 507 - 511.

10
[ 56622-54-9 ]
piperazine-1,2-dicarboxylic acid 1-cyclohexylamide 2-[(6-methyl-pyridin-3-ylmethyl)-amide] [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 507 - 511.

11
[ 56622-54-9 ]
4-cyclohexylcarbamoyl-3-[(6-methyl-pyridin-3-ylmethyl)-carbamoyl]-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 507 - 511.

12
[ 56622-54-9 ]
4-(3-bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-piperazine-1,2-dicarboxylic acid 1-cyclohexylamide 2-[(6-methyl-pyridin-3-ylmethyl)-amide] [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 507 - 511.

13
[ 56622-54-9 ]
[ 1027076-98-7 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2586 - 2593.

14
[ 56622-54-9 ]
[ 177798-41-3 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2586 - 2593.

15
[ 56622-54-9 ]
Acetic acid 5-(acetylamino-methyl)-1-oxy-pyridin-2-ylmethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2586 - 2593.

16
[ 56622-54-9 ]
[ 177798-42-4 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2586 - 2593.

17
[ 56622-54-9 ]
5-(aminomethyl)pyridine-2-carboxaldehyde thiosemicarbazone hydrochloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2586 - 2593.

18
[ 56622-54-9 ]
4-nitro-benzoic acid-(6-methyl-[3]pyridylmethyl ester) [ No CAS ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1936,vol. <2> 146,p. 88,102.

19
[ 4241-27-4 ]
[ 56622-54-9 ]

References: [1]Journal of the American Chemical Society,1947,vol. 69,p. 2574,2577.

20
[ 904309-78-0 ]
[ 56622-54-9 ]
4-amino-5-cyano-6-ethoxy-N-[(6-methylpyridin-3-yl)methyl]pyridine-2-carboxamide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 20h;	6-Methyl-nicotinonitrile (80 mg, 0.7 mmol) and Raney Ni (60 mg, prewashed with methanol) was mixed in 30 mL of ammonia (20% solution in methanol). The heavy walled reaction vessel was charged with H2 (60 psi) and the reaction was shaken at room temperature for 3 h. The mixture was filtered to remove the catalyst, and the filtrate was concentrated to afford an oil (50 mg). This oil was dissolved in 2 mL of anhydrous N,N-dimethylformamide, followed by the addition of 4-amino-5-cyano-6-ethoxy-pyridine-2-carboxylic acid (52 mg, 0.25 mmol), O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate (94 mg, 0.3 mmol), and N,N-diisopropylamine (52 muL, 0.3 mmol). The mixture was stirred at room temperature for 20 h. The crude product was purified via reverse phase HPLC (0-70% CH3CN in 10 mM aq. TFA) to provide 35 mg (45%) of the titled compound as the TFA salt. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.33 (t, J=7.1 Hz, 3H), 2.63 (s, 3H), 4.45-4.60 (m, 4H), 7.05 (s, 1H), 7.34 (bs, 2H), 7.71 (d, J=8.1 Hz, 1H), 8.18 (d, J=8.1 Hz, 1H), 8.64 (s, 1H), 9.18 (t, J=6.3 Hz, 1H). MS (ESI+) m/e=312 (M+H)+.

References: [1]Patent: US2006/173050,2006,A1 .Location in patent: Page/Page column 74.

21
[ 56622-54-9 ]
[ 63139-21-9 ]
[ 916587-13-8 ]

Yield	Reaction Conditions	Operation in experiment
4%	copper diacetate; In 1,2-dichloro-ethane; at 20℃; for 24h;	GP-1b: Synthesis of secondary amines by reaction of a boronic acid with a primary amineThe primary amine 2 is dissolved in dichloroethane. 1.0 eq. copper-(II)-acetate and optionally 1.0 eq. 2.6 lutidine are added followed by boronic acid 1. After stirring for one day at RT, the EPO <DP n="109"/>solvent is removed at the evaporator. After addition of approx. 20-80 ml 2N NaOH solution and approx. 20-80 ml dichloromethane, the white precipitate is removed by centrifugation. The aqueous phase is extracted three times with dichloromethane. The combined organic phases are dried over magnesium sulfate and the solvent is removed under vacuum. The desired secondary amine 3 was obtained, which was used either directly for further reactions or purified by flashchromatography or HPLC.; Step 2:900 mg (7.37 mmol) of the crude compound 2 is reacted according to GP-1B with A- ethylphenylboronic acid (3) without lutidine yielding 788 mg of crude product. After purification by flash chromatography 60.4 mg (0.27 mmol; 4%) of 4 could be obtained.

References: [1]Patent: WO2006/128670,2006,A1 .Location in patent: Page/Page column 107-108; 114.

22
[ 6960-22-1 ]
[ 56622-54-9 ]

Yield	Reaction Conditions	Operation in experiment
58%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 60℃; for 24.75h;	Example 4: Synthesis of 106Step 1 :3.00 g (22.0 mmol) 6-methylnicotinamide is dissolved in 10 ml THF under argon-atmosphere and 34 ml (34 mmol; 1.5 eq.) 1 M lithium aluminum hydride in THF are added. After 45 min additional lithium aluminum hydride (1.22 g; 1.5 eq.) in 40 ml THF is added. The reaction mixture is heated to 60C for 24 h under stirring. The reaction mixture is carefully quenched under stirring with isopropyl alcohol, methanol and finally water at 0C. The solvent is removed under vacuum. After addition of 100 ml 2N NaOH solution and 100 ml DCM the white precipitate is centrifuged off and the aqueous layer is extracted 4 times with 60 ml DCM. The combined organic layers are dried over magnesium sulphate and the solvent is removed under reduced pressure yielding 1.57 g (12.9 mmol; 58%) of the amine 2 which is used without further purification for subsequent reaction steps.

References: [1]Patent: WO2006/128670,2006,A1 .Location in patent: Page/Page column 113.

23
[ 56622-54-9 ]
[ 1651-29-2 ]
[ 1070791-11-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 0 - 100℃; for 13h;	2-Fluoro-N-((6-methylpyridin-3-yl)methyl)-9H-purin-6-amineTo a stirred solution of 6-chloro-2-fluoropurine ( 0.4g, 2.3 mmol) in n-BuOH (50 ml) under an argon atmosphere at O0C, was added DIEA (2.5 ml, 14.7 mmol) followed by <strong>[56622-54-9](6-methylpyridin-3-yl)methanamine</strong> (0.36g, 2.95 mmol). The reaction mixture was stirred at this temperature for 1 h and then allowed to return to room temperature and stirred for 4h, it was still seen incomplete, hence heated the reaction to 1000C and left at that temperature for 8h. The solvent was evaporated in vacuo and the residue was purified by gradient column chromatography on silica gel, eluted with CHCl3 :MeOH (100:0 ? 90:10), to afford the product as a white solid; Yield: 0.38 g (65%) deltaH CDCl3, 250 MHz) 2.44 ( 3 H, s, CH3), 3.66 - 3.57 ( 2 H, m, NHCH2), 4.63 ( 1 H, s, br, NH),7.25 ( 1 H, d, J 7.5, ArH), 7.71 (1 H, dd, J 2.5, 7.5, ArH), 8.14 ( 1 H, s, ArH), 8.49 (1 H, s, ArH), 9.07 (1 H, s, br, NH); deltac ( CDCl3, 250 MHz) 159.12 (C), 158.62 (C), 157.61 (C), 155.56 (C), 147.44 (CH), 146.99 (CH), 136.32 (C), 123.05 (2 x CH), 119.42 (C), 41.64 (CH2), 18.47 (CH3); m/z 259.2 (M + H)

References: [1]Patent: WO2008/122767,2008,A2 .Location in patent: Page/Page column 42.

24
[ 56622-54-9 ]
[ 845866-78-6 ]
[ 13939-06-5 ]
[ 1186519-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene;palladium diacetate; In 1,4-dioxane; at 120℃; for 0.333333h;Sealed tube; Microwave irradiation;	A 5 mL microwave vial was charged with l-bromo-3-iodo-5-(trifluoromethoxy)benzene(98 mg, 0.27 mmol), <strong>[56622-54-9](6-methylpyridin-3-yl)methanamine</strong> (50 mg, 0.41 mmol), molybdenum hexacarbonyl (160 mg, 0.61 mmol), palladium acetate (8 mg, 0.036 mmol), l,8-diazabicyclo[5.4.0]undec- 7-ene (120 mg, 0.79 mmol), and 1,4-dioxane (2 mL). The vial was sealed under nitrogen and the reaction was subjected to microwave irradiation at 120 0C for 20 minutes. After cooling, the mixture was purified via flash chromatography to afford the desired product as a white solid. LC-MS: 391.2 [M+l]+; 1H NMR (CDCl3, 400 MHz): 8.43 (d, J = 2.1 Hz, IH), 7.85 (t, J = 1.5 Hz, IH), 7.63-7.61 (m, 2H), 7.52 (s, IH), 7.16 (d, J = 8.0 Hz, IH), 6.74 (br, IH), 4.60 (d, J = 5.8 Hz, 2H), 2.55 (s, 3H).

References: [1]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 108.

25
[ 56622-54-9 ]
[ 1186518-78-4 ]
[ 1186514-97-5 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	To a mixture of 4'-methyl-5-(methylsulfonyl)biphenyl-3-carboxylic acid (40 mg, 0.14 mmol), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (53 mg, 0.28 mmol), 1- hydroxybenzotriazole hydrate (21 mg, 0.14 mmol), and CH2Cl2 (3 mL) were added (6-methylpyridin-3- yl)methanamine (25 mg, 0.21 mmol), and NN-diisopropylethylamine (48 muL, 0.28 mmol). The mixture was stirred at room temperature overnight and then concentrated. The residue was purified by preparative HPLC (100 x 20.2 mm, Cl 8 column; 30-80% CH3Cnu-water[10 mM Et2NH]) to afford a white solid. LC-MS: 395.5 [M+l]+; 1H NMR (400 MHz, CDCl3): 8.52 (s, IH), 8.34 (s, IH), 8.26 (s, IH), 8.18 (s, IH), 7.65 (dd, IH, J = 8.0, 2.0 Hz), 7.54 (d, 2H, J = 8.0 Hz), 7.30 (d, 2H, J = 8.0 Hz), 7.17 (d, IH, J = 8.0 Hz), 6.73 (bs, IH), 4.66 (d, 2H, J = 5.6 Hz), 3.1 1 (s, 3H), 2.56 (s, 3H), 2.42 (s, 3H).

References: [1]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 86-87.

26
[ 56622-54-9 ]
[ 1186518-79-5 ]
[ 1186515-29-6 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h;	To a mixture of 5-(ethoxycarbonyl)-4'-methylbiphenyl-3-carboxylic acid (1.5 g, 5.3 mmol), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (2.0 g, 10 mmol), 1- hydroxybenzotriazole hydrate (0.32 g, 2.1 mmol), and CH2Cl2 (50 mL) were added (6-methylpyridin-3- yl)methanamine (0.97 g, 7.9 mmol) and NN-diisopropylethylamine (1.8 mL, 10 mmol). The mixture was stirred at room temperature for 4h, and then washed with water and aq. Na2CO3 solution, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel column to afford a white foam. LC-MS: 389.4 [M+l]+; 1H NMR (400 MHz, CDCl3): 8.53 (d, IH, J = 2.0 Hz), 8.39 (t, IH, J = 1.6 Hz), 8.29 (t, IH, J = 1.6 Hz), 8.26 (t, IH, J = 1.6 Hz), 7.66 (dd, IH, J = 8.0, 2.0 Hz), 7.55 (d, 2H, J = 8.4 Hz), 7.28 (d, 2H, J = 8.0 Hz), 7.17 (d, IH, J = 8.0 Hz), 6.64 (m, IH), 4.67 (d, 2H, J = 5.6 Hz), 4.42 (q, 2H, J = 7.2 Hz), 2.57 (s, 3H), 2.41 (s, 3H), 1.42 (t, 3H, J = 7.2 Hz).

References: [1]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 92.

27
[ 56622-54-9 ]
[ 1186518-97-7 ]
[ 1186515-35-4 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	To a mixture of 4'-methyl-5-((6-methylpyridin-3-yl)methylcarbamoyl)-biphenyl-3- carboxylic acid (55 mg, 0.15 mmol), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (58 mg, 0.30 mmol), 1 -hydroxybenzotriazole hydrate (23 mg, 0.15 mmol), and CH2CI2 (3 mL) were added(R)-3-hydroxypyrrolidine (26 mg, 0.30 mmol) and N,N-diisopropylethylamine (53 muL, 0.30 mmol). The mixture was stirred at room temperature overnight, and then concentrated in vacuo. The residue was purified by preparative HPLC (100 x 21.2 mm Cl 8 column, 30-60% MeCnu/water[10 mM Et2NH]) and then silica gel column (0-20% MeOH/CH2Cl2) to afford a white foam.LC-MS: 430.3 [M+l]+; 1H NMR (400 MHz, CD3OD): 8.44 (d, IH, J = 2.0 Hz), 8.19 (m, IH), 7.95-7.90(m, 2H), 7.77 (dd, IH, J = 8.0, 2.4 Hz), 7.59 (d, 2H, J = 8.0 Hz), 7.29 (d, 3H, J = 8.0 Hz), 4.59 (s, 2H),4.50 and 4.37 (m, IH), 3.85-3.30 (m, 4H), 2.51 (s, 3H), 2.38 (s, 3H), 2.20-1.90 (m, 2H).

References: [1]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 94.

28
[ 56622-54-9 ]
[ 1186518-98-8 ]
[ 1186518-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	To a mixture of 3-bromo-5-(methylsulfonyl)benzoic acid (630 mg, 2.2 mmol), N-(3- dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (860 mg, 4.5 mmol), 1 -hydroxybenzotriazole hydrate (140 mg, 0.90 mmol), and CH2Cl2 (25 mL) were added <strong>[56622-54-9](6-methylpyridin-3-yl)methanamine</strong> (550 mg, 4.5 mmol) and NN-diisopropylethylamine (0.79 mL, 4.5 mmol). The mixture was stirred at room temperature overnight, and then diluted with CH2Cl2 (50 mL). The organic phase was washed with water and aq. Na2CO3 solution, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel column (50-100% EtOAc/hexane) to afford a white solid. LC-MS: 385.2 [M+l]+; 1H NMR (400 MHz, CDCl3): 8.51 (d, IH, J = 1.6 Hz), 8.28 (t, IH, J = 1.6 Hz), 8.23 (t, IH, J = 1.6 Hz), 8.19 (t, IH, J = 1.6 Hz), 7.66 (dd, IH, J = 8.0, 2.0 Hz), 7.19 (d, IH, J = 8.0 Hz), 6.93 (bs, IH), 4.63 (d, 2H, J = 5.6 Hz), 3.09 (s, 3H), 2.57 (s, 3H).

References: [1]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 96.

29
[ 56622-54-9 ]
[ 1186519-01-6 ]
[ 1186515-65-0 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	Into a round-bottom flask were charged 3-(5-methylpyridin-2-yl)-5-(pyrrolidine-l - carbonyl)benzoic acid (80 mg, 0.26 mmol), <strong>[56622-54-9](6-methylpyridin-3-yl)methanamine</strong> (60 mg, 0.49 mmol), N- (3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (90 mg, 0.47 mmol), 1- hydroxybenzotriazole hydrate (80 mg, 0.52 mmol), NN-diisopropylethylamine (80 mg, 0.62 mmol) and methylene chloride (5 mL). The mixture was stirred at room temperature overnight and then concentrated. The residue was purified via preparative HPLC to afford the desired product as a white solid.LC-MS: 415.5 [M+l]+; 1H NMR (400 MHz, CD3OD): 8.56 (t, J = 1.7 Hz, IH), 8.53-8.52 (m, IH), 8.46 (d, J = 2.1 Hz, IH), 8.29 (t, J = 1.6 Hz, IH), 8.04 (t, J = 1.6 Hz, IH), 7.89 (d, J = 8.1 Hz, IH), 7.81-7.77 (m, 2H), 7.32 (d, J = 8.0 Hz, IH), 4.63 (s, 2H), 3.66 (t, J = 7.0 Hz, 2H), 3.54 (t, J = 6.7 Hz, 2H), 2.54 (s, 3H),2.43 (s, 3H), 2.05-1.94 (m, 4H).

References: [1]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 97-98.

30
[ 56622-54-9 ]
[ 1186519-05-0 ]
[ 1186516-47-1 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	To a mixture of 4'-bromo-5 -(pyrrol idine-1 -carbonyl)-biphenyl-3-carboxylic acid (1.65 g, 4.41 mmol), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (1.7 g, 8.8 mmol), 1- hydroxybenzotriazole hydrate (0.20 g, 1.3 mmol), and CH2Cl2 (50 mL) were added (6-methylpyridin-3- yl)methanamine (0.81 g, 6.6 mmol) and NN-diisopropylethylamine (1.5 mL, 8.8 mmol). The mixture was stirred at room temperature overnight and then washed with water, dried (Na2SO4), and concentrated. The residue was purified by silica gel column (0-15% MeOHZCH2Cl2) and analytical sample was purified by preparative HPLC (100 x 20.2 mm, Cl 8 column; 30-80% CH3CN-water[10 mM Et2NH]) to afford a white foam.LC-MS: 480.1 [M+l]+; 1H NMR (400 MHz, DMSO-d6): 9.26 (t, IH, J = 5.6 Hz), 8.44 (d, IH, J = 2.0 Hz), 8.23 (t, IH, J = 1.6 Hz), 7.99 (t, IH, J = 1.6 Hz), 7.94 (t, IH, J = 1.6 Hz), 7.77-7.66 (m, 4H), 7.63 (dd, IH, J = 8.0, 2.0 Hz), 7.22 (d, IH, J = 8.0 Hz), 4.49 (d, 2H, J = 5.6 Hz), 3.50 (t, 2H, J = 6.8 Hz), 3.42 (t, 2H, J = 6.8 Hz), 2.44 (s, 3H), 1.93-1.79 (m, 4H).

References: [1]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 104-105.

31
[ 56622-54-9 ]
[ 1186519-15-2 ]
[ 1186516-90-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 25℃; for 16h;	To a solution of 5-(hydroxy-pyridin-2-yl-methyl)-4'-methyl-biphenyl-3-carboxyhc acid (35 mg, 0 11 mmol) in NN-dimethylformamide (1 mL) were added (6-methylpyndin-3-yl)methanamine (40 mg, 0 33 mmol), NNN',N'-tetramethyl-O-(7-azabenzotnazol-l-yl)uronium hexafluorophosphate (100 mg, 0 26 mmol), and NN-diisopropylethylamine (100 muL, 0 57 mmol) The reaction mixture was stirred for 16 hours at 25 0C The reaction mixture was pu?fied by preparative HPLC (100 x 21 2 mmCl 8 column, CH3Cnu/water[10 mM Et2NH]) to afford a light color solidLC-MS 424 1 [M+l] 1H NMR (400 MHz, DMSO-d6) 9 15 (t, IH, J = 5 5 Hz), 8 46 (d, IH, J = 4 0 Hz), 8 41 (bs, IH), 7 99 (bs, IH), 7 88 (bs, IH), 7 83 (bs, IH), 7 79 (t, IH, J = 7 8 Hz), 7 65-7 55 (m, 4H), 7 30 (d, 2H, J = 7 6 Hz), 7 22 (m, 2H), 6 26 (bs, IH), 5 83 (bs, IH), 4 45 (d, 2H, J = 5 4 Hz), 2 43 (s, 3H), 2 35 (s, 3H).

References: [1]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 115.

32
[ 56622-54-9 ]
[ 1186519-17-4 ]
[ 1186516-98-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 25℃; for 16h;	To a solution of 5-(2-methoxyethoxy)-4'-methylbiphenyl-3-carboxylic acid (50 mg, 0.18 mmol) in NN-dimethylformamide (1 mL) were added <strong>[56622-54-9](6-methylpyridin-3-yl)methanamine</strong> (45 mg, 0.37 mmol), N,N,N',N'-tetramethyl-O-(7-azabenzotriazol-l-yl)uronium hexafluorophosphate (150 mg, 0.39 mmol) and N,N-diisopropylethylamine (150 muL, 0.86 mmol). The reaction mixture was stirred for 16 hours at 25 0C. LC-MS indicated the reaction was complete. The reaction mixture was purified by preparative HPLC to afford the title product.LC-MS: 391.5 [M+l]+; 1H NMR (400 MHz, DMSO-d6): 9.13 (t, IH, J = 5.8 Hz), 8.42 (d, IH, J = 2.0 Hz), 7.74 (bs, IH), 7.66-7.60 (m, 3H), 7.40 (bs, IH), 7.34 (bs, IH), 7.29 (d, 2H, J = 8.0 Hz), 7.22 (d, IH, J = 8.0 Hz), 4.47 (d, 2H, J = 5.8 Hz), 4.22 (t, 2H, J = 4.4 Hz), 3.69 (t, 2H, J = 4.4 Hz), 3.32 (s, 3H), 2.44 (s, 3H), 2.35 (s, 3H).

References: [1]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 117.

33
[ 56622-54-9 ]
[ 1186519-26-5 ]
[ 1186517-48-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 25℃; for 16h;	To a solution of 2'-cyano-5-(l,2-dihydroxyethyl)-4'-methylbiphenyl-3-carboxylic acid (30 mg, 0.10 mmol) in NN-dimethylformamide (1 mL) were added <strong>[56622-54-9](6-methylpyridin-3-yl)methanamine</strong> (35 mg, 0.26 mmol), N,NN',N'-tetramethyl-O-(7-azabenzotriazol-l-yl)uronium hexafluorophosphate (100 mg, 0.26 mmol), and NN-diisopropylethylamine (100 muL, 0.57 mmol). The reaction mixture was stirred for 16 hours at 25 0C, and then purified by preparative HPLC to afford the final product as a light color solid.LC-MS: 402.1 [M+l]+; 1H NMR (400 MHz, DMSO-d6): 9.14 (m, IH), 8.47 (bs, IH), 7.94 (m, 2H), 7.79 (bs, IH), 7.70-7.50 (m, 4H), 7.20 (m, IH), 5.46 (bs, IH), 4,80 (bs, IH), 4.66 (bs, IH), 4.46 (bs, 2H), 3.49 (bs, 2H), 2.43 (s, 3H), 2.40 (s, 3H).

References: [1]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 127.

34
[ 56622-54-9 ]
[ 1186519-37-8 ]
[ 1186519-39-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 60℃; for 2h;	Into a round bottom flask were combined 5-formyl-4'-methylbiphenyl-3-carboxylic acid(3.00 g, 12.5 mmol), <strong>[56622-54-9](6-methylpyridin-3-yl)methanamine</strong> (1.91 g, 15.6 mmol), NN-diisopropylethylamine (6.46 g, 49.9 mmol) and NN-dimethylformamide (97 mL). NN,N',N'-Tetramethyl-O-(7-azabenzotriazol- l-yl)uronium hexafluorophosphate (9.50 g, 25.0 mmol) was added in one portion and the mixture was heated at 60 0C for 2 h. After cooling, the mixture was poured onto saturated sodium bicarbonate (200 mL) and extracted with ethyl acetate (3 x 100 mL). The combined extracts were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography using methylene chloride:methanol gradient (0-10%) to afford the title compound. LC-MS: 346.2 [M+l ]+; 1H NMR (400 MHz, DMSO-d6): 10.14 (s, IH), 8.46-8.43 (m, 2H), 8.37-8.33 (m, 2H), 7.72 (d, 2H, J = 8.0 Hz), 7.64 (dd, IH, J = 8.0 Hz), 7.34 (d, 2H, J = 7.9 Hz), 7.22 (d, 2H, J = 7.9 Hz), 4.51 (d, 2H, J = 5.9 Hz), 2.44 (s, 3H), 2.37 (s, 3H).

References: [1]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 136.

35
[ 56622-54-9 ]
[ 188815-32-9 ]
[ 1217484-59-7 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	To a stirred mixture of 3-bromo-5-iodo-benzoic acid (1.4 g, 4.4 mmol), N-(3- dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (1.7 g, 8.8 mmol), 1 -hydroxybenzotriazole hydrate (0.20 g, 1.3 mmol), and CH2Cl2 (50 mL) were added <strong>[56622-54-9](6-methylpyridin-3-yl)methanamine</strong> (0.65 g, 5.3 mmol) and N,N-diisopropylethylamine (1.5 mL, 8.8 mmol). The reaction mixture was stirred at room temperature overnight and then concentrated in vacuo. The precipitated solid was washed with water and ethyl ether and dried to afford the product as a white solid. LC-MS: 432.7 [M+l]+.

References: [1]Patent: WO2010/33168,2010,A2 .Location in patent: Page/Page column 91.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 56622-54-9 ]

Amines

A310850 [3731-52-0]

Pyridin-3-ylmethanamine

Similarity: 0.87

A128370 [823-61-0]

3,6-Dimethyl-2-pyridinamine

Similarity: 0.82

A102178 [20173-04-0]

N-Methyl-1-(pyridin-3-yl)methanamine

Similarity: 0.79

A225171 [387350-39-2]

3-(Aminomethyl)-6-(trifluoromethyl)pyridine

Similarity: 0.76

A211816 [1990-90-5]

3-Methylpyridin-4-amine

Similarity: 0.76

Related Parent Nucleus of
[ 56622-54-9 ]

Pyridines

A310850 [3731-52-0]

Pyridin-3-ylmethanamine

Similarity: 0.87

A128370 [823-61-0]

3,6-Dimethyl-2-pyridinamine

Similarity: 0.82

A102178 [20173-04-0]

N-Methyl-1-(pyridin-3-yl)methanamine

Similarity: 0.79

A225171 [387350-39-2]

3-(Aminomethyl)-6-(trifluoromethyl)pyridine

Similarity: 0.76

A211816 [1990-90-5]

3-Methylpyridin-4-amine

Similarity: 0.76

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.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P231	Handle under inert gas.
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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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.
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P285	In case of inadequate ventilation wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
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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:
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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.
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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:
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P378
P380	Evacuate area.
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P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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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
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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 ...
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Physical hazards
Code	Phrase
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
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
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H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
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
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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

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CAS No.: 56622-54-9

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