Triethylamine → HCID 178425207, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methyl-4-phenoxybenzoic acid (114 mg, 0.5 mmol), o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (285 mg, 0.75 mmol), triethylamine (0.2 mL) and dichloromethane (15 mL) were stirred at 25° C. for half an hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (76 mg, 0.5 mmol) was added. The mixture was stirred at 25° C. for 12 hours. The mixture was washed with water (30 mL). The organic phase was separated, dried over sodium, filtered, concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-3-methyl-4-phenoxybenzamide as a white solid (50 mg, 28%). LRMS (M+H+) m/z: calcd 362.16. found 362. HPLC purity (214 nm): 95%. 1H NMR (300 MHz, d6-DMSO): δ 11.47 (s, 1H), 8.24 (t, J=4.8 Hz, 1H), 8.83 (s, 1H), 7.68 (dd, J=9.6 Hz, J=2.1 Hz, 1H), 7.41-7.35 (m, 2H), 7.13 (t, J=7.5 Hz, 1H), 6.96-6.93 (m, 2H), 6.82 (d, J=8.4 Hz, 1H), 5.80 (s, 1H), 4.29 (d, J=4.8 Hz, 2H), 2.21 (s, 3H), 2.16 (s, 3H), 2.11 (s, 3H).

Provenance & Evidence