Triethylamine → HCID 178425192, compound

Participants

Reaction Steps

4-((Phenylamino)methyl)benzoic acid (150 mg, 0.66 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (301 mg, 0.79 mmol) and triethylamine (2 mL) were dissolved in dichloromethane (20 mL). The mixture was stirred for 0.5 hour. And then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (100 mg, 0.66 mmol) was added to the mixture. 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 N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-((phenylamino)methyl)benzamide (100 mg, 42%). LRMS (M+H+) m/z: calcd 361.18. found 361. HPLC purity (214 nm): 99%. 1H NMR (300 MHz, CD3OD): δ 7.75 (d, J=8.1 Hz, 2H), 7.44 (d, J=8.1 Hz, 2H), 7.06-7.04 (m, 2H), 6.60-6.58 (m, 3H), 6.11 (s, 1H), 4.49 (s, 2H), 4.37 (s, 2H), 2.36 (s, 3H), 2.24 (s, 3H).

Provenance & Evidence