Ammonia → 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide
Reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[NH:9][C:10]1[CH:11]=[C:12]([NH:19][C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=2)[C:13]([C:16]([NH2:18])=[O:17])=[N:14][CH:15]=1.N>CO.O>[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[NH:9][C:10]1[CH:11]=[C:12]([NH:19][C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=2)[C:13]([C:16]([NH2:18])=[O:17])=[N:14][CH:15]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
The 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide hydrochloric acid salt (21.5 g, 50.3 mmol) was diluted with methanol (200 mL) and ammonia (7.0 M solution in methanol, 21.6 mL, 151 mmol). After 30 minutes, the reaction mixture was diluted with water (190 mL) and stirred. After 30 minutes, the reaction mixture was filtered, and the solids were washed with water (2×75 mL) and dried to afford 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide. MS ESI calc'd. for C19H27N6O [M+H]+ 355. found 355. 1H NMR (600 MHz, CD3OD) δ 8.47 (d, J=2.4 Hz, 1H), 7.58 (d, J=2.4 Hz, 1H), 6.58 (s, 1H), 6.47 (s, 1H), 3.61-3.49 (m, 1H), 3.26-3.22 (m, 1H), 2.39 (s, 3H), 2.23 (s, 3H), 1.87-1.55 (m, 6H), 1.49-1.39 (m, 2H).
Workup
- waitAfter 30 minutes
- filtrationthe reaction mixture was filtered
- washthe solids were washed with water (2×75 mL)
- customdried
Sources & evidence
- ORD record
- ord-e27b60cbf0c7452e817794e7b9a9924a
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216173B2
Reaction notes
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