Triethylamine → HCID 178425191, compound

Participants

Reaction Steps

A solution of 2-methyl-4-(1-(piperidin-1-yl)ethyl)benzoic acid (100 mg, 0.40 mmol) in dichloromethane (50 mL) was added 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (35 mg, 0.1 mmol) and triethylamine (32 mg, 0.3 mmol). The mixture was stirred for 30 minutes. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (27 mg, 0.2 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was washed with water (50 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by preparative-TLC (silica gel, methanol/dichloromethane=1:15, 1% NH4OH) to afford N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-4-(piperidin-1-ylmethyl)benzamide as a white solid (35 mg, 23%). LRMS (M+H+) m/z: calcd 381.51. found 381. HPLC purity (214 nm): 93%. 1H NMR (300 MHz, CD3OD): δ 7.42-7.32 (m, 3H), 6.11 (s, 1H), 4.85 (s, 2H), 4.79-4.72 (m, 1H), 2.94-2.79 (m, 4H), 2.40 (s, 3H), 2.34 (s, 3H), 2.24 (s, 3H), 1.83-1.63 (m, 9H).

Provenance & Evidence