Triethylamine → HCID 178425193, compound

Participants

Reaction Steps

To a solution of 4-((methyl(phenyl)amino)methyl)benzoic acid (200 mg, 0.83 mmol) in dichloromethane (50 mL) were added o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (380 mg, 1 mmol) and triethylamine (202 mg, 2 mmol). The mixture was stirred for 0.5 hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (120 mg, 0.8 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) and to afford N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-((methyl(phenyl)amino)methyl)benzamide (50 mg, 16%) as white solid. LRMS (M+H+) m/z: calcd 375.19. found 375. HPLC purity (214 nm): 96%. 1H NMR (300 MHz, CD3OD): δ 7.73 (d, J=8.4 Hz, 2H), 7.29 (d, J=8.1 Hz, 2H), 7.15-7.13 (m, 2H), 6.74-6.70 (m, 3H), 6.10 (s, 1H), 4.57 (s, 2H), 4.47 (s, 2H), 3.01 (s. 3H), 2.35 (s, 3H), 2.23 (s, 3H).

Provenance & Evidence