Triethylamine → HCID 178425170, compound

Participants

Reaction Steps

A solution of 3-fluoro-4-(1-phenoxyethyl)benzoic acid (300 mg, 1.2 mmol) in dichloromethane (15.0 mL) was added N-hydroxybenzotriazole (270 mg, 2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (384 mg, 2 mmol), triethylamine (202 mg, 2 mmol). The mixture was stirred for 30 minutes. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (270 mg, 1.8 mmol) was added and the mixture was stirred at room temperature for 12 hours. To the mixture, water (50 mL) was added. The mixture was extracted with dichloromethane (2*50 mL). The combined organic phase was separated, dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by preparative-TLC (silica gel, methanol/dichloromethane=1:20, 1% NH3) to give 3-fluoro-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-phenoxyethyl)benzamide as white solid (217 mg, 46%). LRMS (M+H+) m/z: calcd 394.17. found 394. HPLC purity (214 nm): 96%. 1H NMR (300 MHz, CD3OD): δ 7.57-7.49 (m, 3H), 7.16 (t, J=8.4 Hz, 2H), 6.85-6.82 (m, 3H), 6.09 (s, 1H), 5.68 (q, J=6.6 Hz, 1H), 4.45 (s, 2H), 2.34 (s, 3H), 2.23 (s, 3H), 1.62 (d, J=8.4 Hz, 3H).

Provenance & Evidence