Triethylamine → HCID 178425702, compound

Participants

Reaction Steps

A mixture of 4-(1-(tetrahydrofuran-3-yloxy)ethyl)benzoic acid (311 mg, 1.32 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (380 mg, 1.98 mmol), N-hydroxybenzotriazole (267.3 mg, 1.98 mmol) and triethylamine (400 mg, 3.96 mmol) in dichloromethane (50 mL) was stirred for 30 minutes at room temperature. Then to the mixture, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (200.64 mg, 1.32 mmol) was added. The resultant mixture was stirred at room temperature for 12 hours. Then the mixture was washed with water (30 mL×3). The organic layer was concentrated to give a residue and the residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-(m-tolyloxy)ethyl)benzamide (452 mg, 92%). LRMS (M+H+) m/z: calcd 370. found 370. 1H NMR (300 MHz, CD3OD): δ 7.78 (d, J=8.4 Hz, 2H), 7.42-7.41 (m, 2H), 6.11 (s, 1H), 4.61-4.58 (m, 1H), 4.49 (s, 2H), 4.07-4.04 (m, 1H), 3.87-3.62 (m, 4H), 2.37 (s, 3H), 2.24 (s, 3H), 1.98-1.87 (m, 2H), 1.40-1.38 (m, 3H)

Provenance & Evidence