Triethylamine → HCID 178425146, compound

Participants

Reaction Steps

To a solution of 4-(2,3-dihydrobenzofuran-2-yl)benzoic acid (0.02 g, 0.08 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.04 g, 0.2 mmol) and N-hydroxybenzotriazole (0.02 g, 0.15 mmol) in dichloromethane (10 mL) was added triethylamine (0.10 g, 1.0 mmol). The reaction mixture was stirred for 15 minutes at room temperature, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (0.03 g, 0.2 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours. After the reaction, the mixture was washed with water. The organic phase was concentrated and the residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1) to give pure product as a white solid 4-(2,3-dihydrobenzofuran-2-yl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (Compound I-51) (0.02 g, 66%). LRMS (M+H+) m/z: calcd 374.16. found 374. 1H NMR (300 MHz, CD3OD): δ 7.80-7.77 (m, 2H), 7.45 (d, J=8.1 Hz, 2H), 7.18-7.12 (m, 2H), 6.87-7.80 (m, 2H), 6.09 (s, 1H), 5.79 (t, J=9.0 Hz, 1H), 4.49 (s, 2H), 3.73-3.64 (m, 1H), 3.14-3.06 (m, 1H), 2.36 (s, 3H), 2.24 (s, 3H).

Provenance & Evidence