Ammonium Hydroxide → 5-[2-(Acetylamino)pyridin-4-yl]-3-(4-chlorobenzyl)-4-cyanothiophene-2-carboxamide

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Reaction Steps

To a solution of 5-[2-(acetylamino)pyridin-4-yl]-3-(4-chlorobenzyl)-4-cyanothiophene-2-carboxylic acid (0.0710 g, 0.172 mmol) in dichloromethane (5.0 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.0991 g, 0.517 mmol) and 1-hydroxybenzotriazole hydrate (0.0528 g, 0.345 mmol). The solution was stirred at room temperature for 30 minutes, then added 33% ammonium hydroxide (33:67 ammonia:water, 0.298 mL, 3.45 mmol) was added. The solution was then stirred at room temperature for 16 hours, then the mixture was concentrated and column chromatography was performed to yield the title compound (0.031 g, 42%). LCMS: (FA) ES+, 411. 1H NMR (400 MHz, d6-DMSO) δ: 10.79 (s, 1H), 8.50-8.46 (m, 2H), 8.14 (br s, 1H), 7.85 (br s, 1H), 7.47-7.43 (m, 1H), 7.39-7.34 (m, 2H), 7.29-7.24 (m, 2H), 4.41 (s, 2H), 2.12 (s, 3H).

Provenance & Evidence