1-Hydroxybenzotriazole → HCID 178425188, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-4-(1-phenoxyethyl)benzoic acid (121 mg, 0.5 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (191 mg, 1 mmol), N-hydroxybenzotriazole (135 mg, 1 mmol), triethylamine (0.2 mL) and dichloromethane (5 mL) were stirred at 25° C. for half an hour. And 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. To the mixture, water (20 mL) was added and the mixture was extracted with dichloromethane (30 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=20:1) to give (S)—N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-phenoxyethyl)benzamide as a white solid (100 mg, 53%). LRMS (M+H+) m/z: calcd. 376.18. found 376. HPLC purity (214 nm): 100%. 1H NMR (300 MHz, d6-DMSO): δ 11.44 (s, 1H), 8.29-8.27 (m, 1H), 7.77 (d, J=8.1 Hz, 2H), 7.42 (d, J=8.1 Hz, 2H), 7.20-7.15 (m, 2H), 6.87-6.83 (m, 3H), 5.83 (s, 1H), 5.53-5.51 (m, 1H), 4.26 (d, J=5.1 Hz, 2H), 2.14 (s, 3H), 2.10 (s, 3H), 1.53 (d, J=6.6 Hz, 3H).

Provenance & Evidence