1-Hydroxybenzotriazole → HCID 178425202, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(3-bromo-2-cyanophenoxy)-3-chlorobenzoic acid (1 g, 2.8 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.08 g, 5.7 mmol), N-hydroxybenzotriazole (769 mg, 5.7 mmol), triethylamine (0.1 mL) and dichloromethane (5 mL) was stirred at 25° C. for half an hour. And then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (430 mg, 2.8 mmol) was added. The mixture was stirred at 25° C. for 12 hours. To the mixture, water (10 mL) was added and the 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=20:1) to give 4-(3-bromo-2-cyanophenoxy)-3-chloro-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide as a white solid (1.1 g, 83%). LRMS (M+H+) m/z: calcd 485.01. found 485. 1H NMR (300 MHz, d6-DMSO): δ 11.44 (s, 1H), 8.52 (s, 1H), 8.12 (s, 1H), 7.90-7.87 (m, 1H), 7.61-7.52 (m, 2H), 7.37 (d, J=6.0 Hz, 1H), 6.86 (d, J=6.3 Hz, 1H), 5.82 (s, 1H), 4.25 (s, 2H), 2.45 (s, 3H), 2.40 (s, 3H).

Provenance & Evidence