1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178425222, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acid (60 mg, 0.25 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (95 mg, 0.5 mmol), N-hydroxybenzotriazole (67 mg, 0.5 mmol), triethylamine (0.1 mL) and dichloromethane (5 mL) were stirred at 25° C. for half an hour before 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (50 mg, 0.33 mmol) was added. The mixture was stirred at 25° C. for 12 hours. To the mixture, was added water (10 ml) 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 vacuum. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxamide as a white solid (28 mg, 29%). LRMS (M+H+) m/z: cald. 377.17. found 377. 1H NMR (300 MHz, d6-DMSO): δ 11.47 (s, 1H), 8.55 (t, J=4.5 Hz, 1H), 7.67 (d, J=6.9 Hz, 1H), 7.38-7.27 (m, 5H), 6.79 (s, 1H), 6.54-6.51 (m, 1H), 6.14 (q, J=7.2 Hz, 1H), 5.85 (s, 1H), 4.23 (d, J=4.5 Hz, 2H), 2.12 (d, J=6.6 Hz, 6H), 1.68 (d, J=7.2 Hz, 3H).

Provenance & Evidence