Triethylamine → HCID 178425172, compound

Participants

Reaction Steps

To a solution of 6-(1-phenoxyethyl)nicotinic acid (100 mg, 0.41 mmol) in dichloromethane (20 mL) were added N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (115 mg, 0.60 mmol), N-hydroxybenzotriazole (81 mg, 0.60 mmol) and triethylamine (122 mg, 1.20 mmol). The resultant reaction mixture was stirred for 30 minutes at room temperature. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (76 mg, 0.50 mmol) was added and the mixture was stirred at ambient temperature overnight. The mixture was washed with brine (20 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified through pre-HPLC and the obtained solution was freeze-dried to afford N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-6-(1-phenoxyethyl)nicotinamide (50 mg, 32.2%) as a white solid. LRMS (M+H+) m/z: calcd 378.17. found 378. 1H NMR (300 MHz, DMSO) δ 8.91 (d, J=2.1 Hz, 1H), 8.14 (dd, J1=8.1 Hz, J2=2.1 Hz, 1H), 7.55 (d, J=8.1 Hz, 1H), 7.17 (m, 2H), 6.85 (m, 3H), 6.10 (s, 1H), 5.45 (m, 1H), 4.48 (s, 2H), 2.35 (s, 3H), 2.24 (s, 3H), 1.64 (d, J=6.6 Hz, 3H).

Provenance & Evidence