Triethylamine → HCID 178482202, compound

Participants

Reaction Steps

To a solution of 4-phenoxybenzoic acid (54 mg, 0.25 mmol) in dichloromethane (15 mL) were added 1-Hydroxybenzotriazole (49 mg, 0.36 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (69 mg, 0.36 mmol) and triethylamine (73 mg, 0.72 mmol). The resulting solution was stirred at room temperature for 30 minutes. Then 3-(aminomethyl)-6-methyl-4-(methylamino) pyridin-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 to provide crude product which was purified by silica gel column chromatography with dichloromethane/methanol=10:1 to afford N-((2-hydroxy-6-methyl-4-(methylamino)pyridin-3-yl)methyl)-4-phenoxybenzamide (10 mg, 11% yield) as a white solid. LRMS (M+H+) m/z: calcd 364.16. found 364. HPLC Purity (214 nm): 98%. 1H NMR (300 MHz, CD3OD): δ 7.78-7.81 (d, J=8.7 Hz, 2H), 7.37-7.43 (m, 2H), 7.20 (d, J=7.5 Hz, 1H), 6.97-7.06 (m, 4H), 5.90 (s, 1H), 4.40 (s, 2H), 2.90 (s, 3H), 2.23 (s, 3H).

Provenance & Evidence