3-Pyridinecarboxamide,2-methyl-(9CI) Chemical Properties

Melting point:

158 °C

Boiling point:

271.9±28.0 °C(Predicted)

Density 

1.157±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

14.85±0.50(Predicted)

color 

White to Off-White

Safety Information

HS Code 

2933399990

3-Pyridinecarboxamide,2-methyl-(9CI) Usage And Synthesis

Chemical Properties

White solid

Uses

2-Methylnicotinamide (~12% inorganics) can be used as JAK inhibitors to treat autoimmune disease or cancer.

Definition

ChEBI: 2-methylnicotinamide is a pyridinecarboxamide that is nicotinamide substituted by a methyl group at C-2. It has a role as a metabolite. It is functionally related to a nicotinamide.

Synthesis

General procedure for the synthesis of 2-methylnicotinamide from 2-methylnicotinic acid: 2-methylnicotinic acid (0.537 mg, 3.9 mmol) was dissolved in 20 mL of DMF at 0 °C, and HATU (1.56 g, 4.1 mmol) and DIPEA (0.72 mL, 4.1 mmol) were added sequentially. Subsequently, ammonia (NH3) was passed into the reaction system for 15 min. The reaction mixture was stirred overnight at room temperature. After completion of the reaction, the paste was obtained by filtration, washed with cold DMF and the filtrate was discarded. The mother liquor was concentrated and purified by normal phase chromatography with the eluent being MeOH solution of CH2Cl2/7N NH3 (93:7, v/v). The final white solid product 2-methylnicotinamide (405 mg, 76% yield) was obtained. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 1.34 (s, 9H), 1.36 (d, J = 6.64 Hz, 3H), 2.56 (s, 3H), 4.32-4.40 (m, 1H), 7.15-7.19 (m, J = 8.20 Hz, 1H), 7.68 (d, J = 8.20 Hz, 1H) .

References

[1] Patent: WO2007/73303, 2007, A2. Location in patent: Page/Page column 38
[2] Patent: EP1193265, 2002, A2. Location in patent: Page 76-77
[3] Patent: US2013/281397, 2013, A1. Location in patent: Paragraph 0438; 0439
[4] Journal of Medicinal Chemistry, 2000, vol. 43, # 16, p. 3168 - 3185
[5] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 58 - 66,9

3-Pyridinecarboxamide,2-methyl-(9CI)(58539-65-4)Related Product Information

• 5H-Pyrrolo[3,4-b]pyridine-5,7(6H)-dione
• 5-OXO-N-(3-PYRIDINYLMETHYL)-2-(TRIFLUOROMETHYL)-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• 2-(DIMETHYLAMINO)-1H-CHROMENO[2,3-B][1,6]NAPHTHYRIDINE-1,11(2H)-DIONE
• N-(4-CHLOROBENZYL)-2-METHYL-5-OXO-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• N-(TERT-BUTYL)-2-METHYL-5-OXO-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• N-METHYL-5-OXO-2-(TRIFLUOROMETHYL)-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• 2-METHYL-5-OXO-N-[3-(TRIFLUOROMETHYL)PHENYL]-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• 5-OXO-2-(TRIFLUOROMETHYL)-N-[3-(TRIFLUOROMETHYL)PHENYL]-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• N-(4-CHLOROBENZYL)-5-OXO-2-(TRIFLUOROMETHYL)-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• 5-OXO-N-(2-PYRIDINYLMETHYL)-2-(TRIFLUOROMETHYL)-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• N-ALLYL-5-OXO-2-(TRIFLUOROMETHYL)-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• N-BENZYL-2-METHYL-5-OXO-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• N-(2,6-DIMETHYLPHENYL)-5-OXO-2-(TRIFLUOROMETHYL)-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• 2-METHYL-10-OXO-10H-9-OXA-1-AZA-ANTHRACENE-3-CARBOXYLIC ACID ALLYLAMIDE
• 1H-CHROMENO[2,3-B][1,6]NAPHTHYRIDINE-1,11(2H)-DIONE
• N-(2,4-DIFLUOROPHENYL)-5-OXO-2-(TRIFLUOROMETHYL)-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• N-(4-CHLOROPHENYL)-2-METHYL-5-OXO-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE
• 5-OXO-2-(TRIFLUOROMETHYL)-N-[3-(TRIFLUOROMETHYL)BENZYL]-5H-CHROMENO[2,3-B]PYRIDINE-3-CARBOXAMIDE