Triethylamine → HCID 178436442, compound

Participants

Reaction Steps

To a solution of 4-(2-cyano-3-ethylphenoxy)-3-methylbenzoic acid (0.10 g, 0.36 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.10 g, 0.5 mmol) and N-hydroxybenzotriazole (0.07 g, 0.5 mmol) in dichloromethane (20 mL) was added triethylamine (0.4 g, 4 mmol). The reaction mixture was stirred at room temperature for 15 minutes, then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (0.06 g, 0.4 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours. After the reaction, the mixture was washed with water (30 mL). The organic phase was concentrated and purified by column chromatography (silica gel, dichloromethane/methanol=15:1) to give pure product 4-(2-cyano-3-ethylphenoxy)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-3-methylbenzamide as a white solid (0.062 g, 41%). LRMS (M+H+) m/z: calcd 415.19. found 415. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.31 (d, J=4.5 Hz, 1H), 7.86 (s, 1H), 7.75 (s, 1H), 7.72 (s, 1H), 7.05-6.70 (m, 2H), 6.80 (dd, J=8.4 Hz, J=2.4 Hz, 1H), 5.85 (s, 1H), 4.29 (d, J=4.5 Hz, 2H), 2.74 (q, J=7.5 Hz, 2H), 2.16 (s, 3H), 2.14 (s, 3H), 2.10 (s, 3H), 1.17 (t, J=7.5 Hz, 3H).

Provenance & Evidence