Triethylamine → HCID 178425203, compound

Participants

Reaction Steps

4-(2-Bromophenoxy)-3-chlorobenzoic acid (174 mg, 0.53 mmol), 1-hydroxybenzotriazole (108 mg, 0.8 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (154 mg, 0.8 mmol), triethylamine (0.4 mL, 2.88 mmol) were dissolved in dichloromethane (20 mL). The mixture was stirred at room temperature for 0.5 hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (100 mg, 0.66 mmol) was added to the solution. The mixture was stirred at room temperature for 12 hours. To the mixture, water (20 mL) was added and the resultant mixture was extracted with dichloromethane (10 mL×3). The combined organic phase was separated, dried by sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give 4-(2-bromophenoxy)-3-chloro-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide as a white solid (190 mg, 78%). LRMS (M+H) m/z: calcd 460.02. found 460. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.44 (t, J=4.5 Hz, 1H), 8.09 (d, J=1.8 Hz, 1H), 7.81-7.75 (m, 2H), 7.46-7.40 (m, 1H), 7.23-7.17 (m, 1H), 7.10 (dd, J=6.9 Hz, J=1.2 Hz, 1H), 6.83 (d, J=8.4 Hz, 1H), 5.85 (s, 1H), 4.27 (d, J=4.5 Hz, 2H), 2.15 (s, 3H), 2.10 (s, 3H).

Provenance & Evidence