| Identification | Back Directory | [Name]
3-Pyridinecarboxamide,2-methyl-(9CI) | [CAS]
58539-65-4 | [Synonyms]
2-methylnicotinamide
2-Methyl-3-PyridinecarboxaMide
3-Pyridinecarboxamide, 2-methyl-
3-Pyridinecarboxamide,2-methyl-(9CI)
2-Methylnicotinamide (~12% inorganics)
3-Pyridinecarboxamide,2-methyl-(9CI) ISO 9001：2015 REACH | [EINECS(EC#)]
-0 | [Molecular Formula]
C7H8N2O | [MDL Number]
MFCD09909457 | [MOL File]
58539-65-4.mol | [Molecular Weight]
136.15 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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