Ammonia → 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide

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Reaction Steps

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).

Provenance & Evidence