| Identification | Back Directory | [Name]
3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE | [CAS]
910543-72-5 | [Synonyms]
3-Amino-5-bromo-1-methylp...
3-amino-5-bromo-1-methyl-2-pyridinone
3-Amino-5-bromo-1-methylpyridin-2-one
3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE
3-amino-5-bromo-1-methyl-2(1H)-Pyridinone
l-Methyl-3-aMino-5-broMo-l-H-pyridin-2-one
2(1H)-Pyridinone, 3-amino-5-bromo-1-methyl-
3-amino-5-bromo-1-methyl-1,2-dihydropyridin-2-one | [Molecular Formula]
C6H7BrN2O | [MDL Number]
MFCD09835082 | [MOL File]
910543-72-5.mol | [Molecular Weight]
203.04 |
| Chemical Properties | Back Directory | [Boiling point ]
258.7±40.0 °C(Predicted) | [density ]
1.713±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [pka]
2?+-.0.20(Predicted) | [Appearance]
Light brown to brown Solid |
| Hazard Information | Back Directory | [Uses]
3-Amino-5-bromo-1-methylpyridin-2(1H)-one is a useful reagent used in the preparation of novel 5-phenylpyridin-2(1H)-one derivatives as potent reversible Bruton''s tyrosine kinase inhibitors with antiarthritic activity for the treatment of Rheumatoid arthritis. | [Synthesis]
General procedure for the synthesis of 3-amino-5-bromo-1-methyl-3-nitropyridin-2(1H)-one from 5-bromo-1-methyl-3-nitropyridin-2(1H)-one: To a 1-liter three-necked round-bottomed flask fitted with a mechanical stirrer and a reflux condenser, under nitrogen protection, was added 5-bromo-1-methyl-3-nitropyridin-2(1H)-one (21.7 g, 93.3 mmol) , ethanol (305 mL), iron powder (-325 mesh, 52.1 g, 933 mmol) and 2N hydrochloric acid (50 mL, 100 mmol). The reaction mixture was heated and stirred at 60°C for 2 hours. After completion of the reaction, it was cooled to room temperature and the pH was adjusted to 8 (measured by pH paper) by adding potassium carbonate. The resulting suspension was filtered and the filter cake was washed with ethanol (4 x 100 mL). The filtrates were combined and concentrated under reduced pressure to give a brown solid. The solid was purified by silica gel column chromatography to afford the target product 3-amino-5-bromo-1-methylpyridin-2(1H)-one (14.5 g, 77% yield) as an off-white powder with a melting point of 104-105 °C. 1H NMR (500 MHz, DMSO-d6) δ 7.15 (d, 1H, J = 2.5 Hz), 6.46 (d, 1H, J = 2.5 Hz), 5.45 (bs, 2H), 3.40 (s, 3H); MS (ESI+) m/z 203 (M+H). | [References]
[1] Organic Process Research and Development, 2014, vol. 18, # 1, p. 228 - 238
[2] Patent: US2009/82330, 2009, A1. Location in patent: Page/Page column 39-41
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 11, p. 3021 - 3029
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 755 - 758
[5] Patent: WO2006/99268, 2006, A2. Location in patent: Page/Page column 69 |
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