Triethylamine → HCID 178428519, compound

Participants

Reaction Steps

To a solution of 4-phenoxybenzoic acid (196 mg, 0.91 mmol) in dichloromethane (15 mL) were added 1-hydroxybenzotriazole (177 mg, 1.3 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (251 mg, 1.3 mmol) and triethylamine (265 mg, 2.6 mmol). The resulting solution was stirred at room temperature for 30 minutes. Then 4-amino-3-(aminomethyl)-6-methylpyridin-2-ol (200 mg, 1.3 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-((4-amino-2-hydroxy-6-methylpyridin-3-yl)methyl)-4-phenoxybenzamide (180 mg, 57% yield) as a white solid. LRMS (M+H+) m/z: calcd 350.14. found 350. HPLC Purity (214 nm): 97%. 1H NMR (300 MHz, CDCl3): δ 10.71 (d, J=2.4 Hz, 1H), 7.76-7.79 (d, J=8.7 Hz, 2H), 7.32-7.38 (m, 2H), 7.12-7.17 (m, 1H), 6.94-7.02 (m, 4H), 5.64-5.65 (br, 1H), 5.51 (s, 1H), 4.47-4.49 (d, J=6.6 Hz, 2H), 3.48 (s, 2H), 2.16 (s, 3H).

Provenance & Evidence