Hydrochloric Acid → HCID 86703293, compound

Participants

Reaction Steps

Under an argon atmosphere, to a suspension of 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylic acid (100 mg) in dichloromethane (2.8 mL) were added cyanamide (12.9 mg), 4-dimethylaminopyridine (75 mg), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (118 mg) successively, and this mixture was stirred at room temperature for 60 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid, water, and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane) to obtain the title compound (73.1 mg). 1H-NMR (DMSO-d6) δ ppm: 3.78 (3H, s), 4.47 (2H, s), 6.64 (1H, dd, J=2.3, 8.8 Hz), 6.89 (1H, d, J=2.3 Hz), 7.18-7.39 (3H, m), 7.42-7.52 (2H, m), 7.56-7.68 (2H, m), 7.84-7.99 (2H, m), 11.24 (1H, s). ESI-MS (m/z): 383 (M+H)+

Provenance & Evidence