1-Hydroxybenzotriazole → HCID 178425197, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methyl-4-(phenoxymethyl)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 N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-3-methyl-4-(phenoxymethyl)benzamide (Compound I-54) as a white solid (51 mg, 26%). LRMS (M+H+) m/z: calcd 376.45. found 376. HPLC purity (214 nm): 99%. 1H NMR (300 MHz, d6-DMSO): δ 11.43 (s, 1H), 8.29 (t, J=4.2 Hz, 1H), 7.69-7.63 (m, 2H), 7.43 (d, J=8.1 Hz, 1H), 7.29 (t, J=7.5 Hz, 2H), 7.03-6.91 (m, 3H), 5.85 (s, 1H), 5.11 (s, 2H), 4.29 (d, J=4.8 Hz, 2H), 2.34 (s, 3H), 2.17 (s, 3H), 2.11 (s, 3H).

Provenance & Evidence