Triethylamine → HCID 178425205, compound

Participants

Reaction Steps

To a solution of 2-methyl-4-phenoxybenzoic acid (100 mg, 0.44 mmol) in dichloromethane (20 mL) were added o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (190 mg, 0.5 mmol), and triethylamine (77 mg, 0.7 mmol). The mixture was stirred for 0.5 hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (60 mg, 0.4 mmol) was added and the mixture was stirred at room temperature for 4 hours. The mixture was washed with water (50 mL) and the organic phase was separated, concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to afford N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-4-phenoxybenzamide (40 mg, 25%) as a white solid. LRMS (M+H+) m/z: calcd 362.16. found 362. HPLC purity (214 nm): 100%. 1H NMR (300 MHz, d6-DMSO): δ 7.40-7.31 (m, 3H), 7.18-7.13 (m, 1H), 7.02-6.99 (m, 2H), 6.83-6.76 (m, 2H), 6.12 (s, 2H), 4.47 (s, 2H), 2.43 (s, 3H), 2.41 (s, 3H), 2.20 (s, 3H).

Provenance & Evidence