Triethylamine → HCID 178494488, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(methoxy(phenyl)methyl)benzoic acid (0.26 g, 1.07 mmol), 1-ethyl-3-(3-dimethyl aminopropyl)carbodiimide hydrochloride (309 mg, 1.61 mmol), 1-hydroxybenzotriazole (218 mg, 1.61 mmol), triethylamine (0.45 mL) and dichloromethane (15 mL) was stirred at 25° C. for half an hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (163 mg, 1.07 mmol) was added. The mixture was stirred at 25° C. for 12 hours. The resultant mixture was 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)-4-(methoxy(phenyl)methyl)benzamide (Compound I-53) as a white solid (80 mg, 20%). LRMS (M+H+) m/z: calcd 376.18. found 376. HPLC purity (214 nm): 96%. 1H NMR (300 MHz, d6-DMSO): δ 11.43 (s, 1H), 8.25 (t, J=3.6 Hz, 1H), 7.30 (d, J=6.9 Hz, 2H), 7.41-7.18 (m, 7H), 5.95 (s, 1H), 5.83 (s, 1H), 4.27 (d, J=3.6 Hz, 2H), 3.31 (s, 3H), 2.14 (s, 3H), 2.10 (s, 3H).

Provenance & Evidence