N-(4-amino-5-cyano-6-isopropoxypyridin-2-yl)-2-(2,5-dimethoxyphenyl)acetamide → N-[4-amino-5-cyano-6-(2-methoxyethoxy)pyridin-2-yl]-2-(2,5-dimethoxyphenyl)acetamide

Participants

Reaction Steps

To a solution of 42 mg (0.20 mmol) of 4,6-diamino-2-(2-methoxy-ethoxy)-nicotinonitrile in 0.2 mL of pyridine and 1 mL of CH2Cl2 was added 75 mg (0.35 mmol) of 2,5-dimethoxyphenylacetyl chloride (Example 60B). The mixture was stirred at ambient temperature for 10 minutes then diluted with 1 mL of water and concentrated under reduced pressure. The residue was dissolved in 1 mL of ethyl acetate, then extracted with water (1×10 mL), 1M HCl(aq.) (2×5 mL), saturated NaHCO3(aq.) (2×5 mL), and brine (1×5 mL), dried over MgSO4, filtered, and concentrated to a yellow solid. The residue was recrystallized from 3 mL of ethyl acetate to provide 30 mg (38%) of a white solid. 1H NMR (300 MHz, d6-DMSO) δ 10.11 (s, 1H), 7.14 (s, 1H), 6.90 (m, 3H), 6.79 (m, 2H), 4.42 (m, 2H), 3.70 (s, 3H), 3.69 (s, 3H), 3.64 (m, 4H), 3.31 (s, 3H); MS (ESI) m/e=329 (M-CH2CH2OCH3+H)+, 387 (M+H)+, 385 (M−H)−.

Provenance & Evidence