Methanamine, N-methoxy-, hydrochloride (1:1) → 8-chloro-5-(3-fluorophenyl)-N-methoxy-N-methylimidazo[1,5-a]pyridine-6-carboxamide

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Reaction Steps

8-Chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-carboxylic acid (0.29 g, 1.0 mmol) was stirred in N,N-dimethylformamide (2.8 mL). N,N-Diisopropylethylamine (0.87 mL, 5.0 mmol), N,O-dimethylhydroxylamine hydrochloride (0.29 g, 3.0 mmol) and a solution of 0.6 N 1-hydroxy-7-azabenzotriazole in N,N-dimethylformamide (0.33 mL, 0.2 mmol) were added. The mixture was stirred for 5 minutes and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.29 g, 1.5 mmol) was added. The mixture was stirred for 2 hours. The mixture was poured into saturated sodium bicarbonate and extracted into ethyl acetate 3×. The ethyl acetate extracts were combined and washed with water, dried over sodium sulfate, filtered, concentrated and purified by flash column chromatography with ethyl acetate in hexanes (0-80%) to give the desired compound (0.20 g, 60%). LCMS calculated for C16H14ClFN3O2 (M+H)+: m/z=334.1. found: 333.9. 1H NMR (300 MHz, DMSO-d6): δ 8.10 (s, 1H), 7.60 (m, 2H), 7.42 (m, 3H), 7.20 (s, 1H), 3.41 (br s, 3H), 3.00 (s, 3H).

Provenance & Evidence