Triethylamine → HCID 178425151, compound

Participants

Reaction Steps

2-methyl-4-(1-phenylethyl)benzoic acid (150 mg, 0.6 mmol) was dissolved in 20 mL dichloromethane, and then N-hydroxybenzotriazole (0.9 mmol, 100 mg), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.9 mmol, 200 mg), triethylamine (10.48 mmol, 3 mL) was added to the mixture. After the mixture was stirred at room temperature for 10 minute, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (0.6 mmol, 90 mg) was added. The mixture was stirred at room temperature for 18 hours. Then washed with water (30 mL), extracted with dichloromethane (40 mL). The organic layer were concentrated and subjected to column chromatography (silica gel, dichloromethane/menthol=15/1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-phenylethyl)benzamide (150 mg, 90%). 1H NMR (300 MHz, CD3OD): δ 7.25-7.05 (m, 8H), 6.08 (s, 1H), 4.44 (s, 2H), 4.09 (m, 1H), 2.35 (s, 3H), 2.31 (s, 3H), 2.23 (s, 3H) 1.59 (d, J=8.4 Hz, 3H); LRMS (M+H+) m/z: calcd 374.20. found 374.

Provenance & Evidence