Triethylamine → HCID 178425152, compound

Participants

Reaction Conditions

Reaction Steps

4-Phenethylbenzoic acid (30 mg, 0.13 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (103 mg, 0.27 mmol) was dissolved in dichloromethane (20 mL), and then added triethylamine (2 mL) was added. After the mixture were stirred at 25° C. for 0.5 hour, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (20 mg, 0.13 mmol) was added. The mixture was stirred at 25° C. for 12 hours. To the mixture, water (15 ml) was added. And the mixture was extracted with dichloromethane (10 mL×3). The combined organic phase was separated, dried by sodium sulfate and then filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-phenethylbenzamide (10 mg, 21%). LRMS (M+H+) m/z: calcd 360.18. found 360. HPLC purity (214 nm): 94%. 1H NMR (300 MHz, CD3OD): δ 7.67 (d, J=8.7 Hz, 2H), 7.24-7.12 (m, 7H), 6.10 (s, 1H), 4.48 (s, 2H), 2.95-2.91 (m, 4H), 2.36 (s, 3H), 2.24 (s, 3H).

Provenance & Evidence