3-Aminopropionitrile → HCID 178425214, compound

Participants

Reaction Steps

To a solution of 4-(benzyloxy)benzoic acid (228 mg, 1 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (210 mg, 1.1 mmol) and hydroxybenzotriazole (149 mg, 1.1 mmol) in dichloromethane (30 mL) was added triethylamine (202 mg, 2 mmol). The reaction mixture was stirred at room temperature for 1 hour, then 3-aminopropanenitrile (156 mg, 1 mmol) was added. The reaction mixture was stirred at room temperature overnight. After the reaction, the mixture was washed with saturated solution of sodium bicarbonate (10 mL×3), dried over anhydrous sodium sulfate to give crude product which was purified by column chromatography (silica gel, dichloromethane/methanol=50:1) to give 4-(benzyloxy)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (Compound I-12) (110 mg, 30%). LRMS (M+H+) m/z: calcd 451.11. found 451. 1H NMR (300 MHz, d6-DMSO) δ11.47 (s, 1H), 8.20 (s, 1H), 7.82 (d, J=8.7 Hz, 2H), 7.49-7.35 (m, 5H), 7.05 (d, J=8.7 Hz, 2H), 5.88 (s, 1H), 5.17 (s, 1H), 4.30 (d, J=4.8 Hz, 2H), 2.19 (s, 1H), 2.13 (s, 1H).

Provenance & Evidence