Pyridine → N-(4-amino-5-cyano-6-propylpyridin-2-yl)-2-(2,5-dimethoxyphenyl)acetamide

Beteiligte Stoffe

Reaktionsschritte

To a solution of 23 mg (0.13 mmol) of 4,6-diamino-2-propyl-nicotinonitrile (Example 68B) and 50 mg (0.63 mmol) of pyridine in 1 mL of CH2Cl2 was added 35 mg (0.16 mmol) of (2,5-dimethoxyphenyl)acetyl chloride (Example 68A). The mixture was stirred at ambient temperature for 10 minutes then diluted with 3 mL of water. The mixture was extracted with ethyl acetate (3×3 mL), then the combined ethyl acetate layers were back extracted with saturated NaHCO3(aq.) (1×3 mL), and brine (1×3 mL), dried over MgSO4, filtered, and concentrated to an oil. This was suspended in 5 mL of toluene, then concentrated under reduced pressure to remove some pyridine. The product was purified via silica gel chromatography, eluting with 60:40 ethyl acetate:hexanes to provide 21 mg (46%) of a white solid. 1H NMR (300 MHz, d6-DMSO) δ 10.27 (s, 1H), 7.34 (s, 1H), 6.83 (m, 5H), 3.70 (m, 6H), 3.65 (s, 2H), 2.64 (m, 2H), 1.68 (m, 2H), 0.93 (t, 3H, J=7.3 Hz); MS (ESI) m/e 355 (M+H)+, 353 (M−H)−.

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