1,2-Dichloroethane → 3-Butyl-imidazo[1,5-a]pyridine-1-carboxylic acid adamantan-1-ylamide

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Reaction Steps

To a solution of 3-butyl-imidazo[1,5-a]pyridine-1-carboxylic acid (150 mg, 0.56 mmol) in DMF (5 mL) was added EDC (161 mg, 0.84 mmol), HOBt, (90 mg, 0.67 mmol) and Et3N (0.23 mL, 1.68 mmol). The mixture was allowed to stir for 10 min. and adamantylamine (93 mg, 0.62 mmol) was added. The mixture was stirred for 15 h then diluted with ethyl acetate (30 mL) and washed with water (50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica to yield the title compound (157 mg, 80%). 1H NMR (DMSO-d6) δ 8.31 (1H), 8.02 (1H), 7.04 (1H), 6.93 (1H), 6.81 (1H), 2.99 (2H), 2.08 (9H), 1.67 (8H), 1.38 (2H), 0.92 (3H); m/z (M+H)=352.1.

Provenance & Evidence