1,2-Dichloroethane → 3-(2-Morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine-1-carboxylic acid phenylamide

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Reaction Steps

To a solution of 3-butyl-imidazo[1,5-a]pyridine-1-carboxylic acid (200 mg, 0.73 mmol) in DMF (5 mL) was added EDC (182 mg, 0.95 mmol), HOBt, (129 mg, 0.95 mmol) and iPr2EtN (0.22 mL, 1.31 mmol). The mixture was allowed to stir for 10 min. and aniline (0.080 mL, 0.88 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 (40 mg, 16%). 1H NMR (DMSO-d6) δ 9.72 (1H), 8.41 (1H), 8.15 (1H), 7.83 (2H), 7.30 (2H), 7.18 (1H), 7.05 (1H), 6.95 (1H), 3.58 (4H), 3.25 (2H), 2.80 (2H), 2.48 (4H); m/z (M+H)=351.15.

Provenance & Evidence