Triethylamine → HCID 178492317, compound

Participants

Reaction Steps

To a solution of 2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acid (97 mg, 0.40 mmol) in dichloromethane (15 mL) were added 1-Hydroxybenzotriazole (73 mg, 0.54 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (104 mg, 0.54 mmol) and triethylamine (111 mg, 1.1 mmol). The resultant solution was stirred at room temperature for 30 minutes. Then 3-(aminomethyl)-4-methoxy-6-methylpyridin-2-ol (60 mg, 0.36 mmol) was added to the solution, and it was stirred at room temperature for 16 hours. Water (20 mL) was added to the mixture. It was extracted with dichloromethane (50 mL). The organic layer was concentrated in vacuo to provide crude product which was purified by silica gel column chromatography with dichloromethane/methanol=10:1 to afford N-((2-hydroxy-4-methoxy-6-methylpyridin-3-yl)methyl)-2-oxo-1-(1-phenylethyl)-1,2-dihydro pyridine-4-carboxamide (40 mg, 28% yield) as a white solid. 1H NMR (300 MHz, CD3OD): δ 7.56 (d, J=7.2 Hz, 1H), 7.31-7.39 (m, 5H), 6.86 (d, J=1.8 Hz, 1H), 6.60 (br, 1H), 6.25-6.30 (m, 2H), 4.41 (s, 2H), 3.91 (s, 3H), 2.31 (s, 3H), 1.76 (d, J=7.2 Hz, 3H).

Provenance & Evidence