Triethylamine → HCID 178425209, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(2-cyanophenoxy)benzoic acid (500 mg, 2.09 mmol), 1-ethyl-3-(3-dimethyl aminopropyl)carbodiimide hydrochloride (453 mg, 2.37 mmol), N-hydroxybenzotriazole (320 mg, 2.37 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 (318 mg, 2.09 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-(2-cyanophenoxy)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide as a white solid (400 mg, 51%). LRMS (M+H+) m/z: calcd 373.14. found 373. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.38 (s, 1H), 7.94-7.91 (m, 3H), 7.69 (t, J=8.1 Hz, 1H), 7.37-7.31 (m, 1H), 7.16-7.06 (m, 3H), 5.86 (s, 1H), 4.29 (d, J=4.2 Hz, 2H), 2.17 (s, 3H), 2.11 (s, 3H).

Provenance & Evidence