Triethylamine → N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-isopropoxyethyl)benzamide

Participants

Reaction Steps

To the solution of 4-(1-isopropoxyethyl)benzoic acid (137 mg, 0.66 mmol) in dichloromethane (80 mL) was added o-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (380 mg, 1 mmol) and triethylamine (200 mg, 2 mmol). then the 3-(aminomethyl)-4,6-di methylpyridin-2-ol (100 mg, 0.66 mmol) was added, the solution was stirred at room temperature for 12 hours, water (80 mL) was added and washed 3 times, the organic layer was evaporated and purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-isopropoxyethyl)benzamide (57 mg, 91%) LRMS (M+H+) m/z: calcd: 342.19. found 342; 1H-NMR (300 MHz, CD3OD) 1H-NMR (300 MHz, CD3OD) δ 7.77 (d, J=8.4 Hz, 2H), 7.40 (d, J=8.4 Hz, 2H), 6.10 (s, 1H), 4.64-4.62 (m, 1H), 4.49 (s, 2H), 3.52-3.48 (m, 1H), 2.36 (s, 3H), 2.24 (s, 3H), 1.36 (d, J=6.3 Hz, 3H), 1.15 (d, J=6 Hz, 3H), 1.06 (d, J=6 Hz, 3H).

Provenance & Evidence