Triethylamine → HCID 178425156, compound

Participants

Reaction Steps

A mixture of 4-(3-Methyl-1-phenoxybutyl)benzoic acid (20 mg, 0.07 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (59 mg, 0.15 mmol) and triethylamine (2 mL) was dissolved in dichloromethane (20 mL). The mixture was stirred for 0.5 hour. And then added 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (100 mg, 0.66 mmol) was added to the mixture and the resultant mixture was stirred at 25° C. for 12 hours. To the mixture, water (10 mL) was added and the reaction mixture was extracted with dichloromethane (10 mL×3). The combined organic phase was dried by sodium sulfate and then filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(3-methyl-1-phenoxybutyl)benzamide (Compound I-49) (15 mg, 52%). LRMS (M+H+) m/z: calcd 418.23. found 418. HPLC purity (214 nm): 95%. 1H NMR (300 MHz, CD3OD): δ 7.73 (d, J=8.4 Hz, 2H), 7.42 (d, J=8.1 Hz, 2H), 7.13 (t, J=7.5 Hz, 2H), 6.83-6.79 (m, 3H), 6.09 (s, 1H), 5.26-5.21 (m, 1H), 4.47 (s, 2H) 2.34 (s, 3H), 2.23 (s, 3H), 1.95-1.82 (m, 2H), 1.61-1.56 (m, 1H), 1.02-0.95 (m, 6H).

Provenance & Evidence