Hydrogen Sulfide → HCID 60064160, compound

Participants

Reaction Steps

Hydrogen sulfide was blown into a solution of (S)-2-[N-[4-(1-tert-butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonylbenzoyl)-aminomethyl]-5-cyano-1-(1-phenylethylcarbamoylmethyl)benzimidazole (284 mg) in a mixture of pyridin-triethylamine (5:1) (10 ml) with ice-cooling, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was evaporated and the residue was treated with hydrogen chloride-ethanol. Thereto were added acetone (6 ml), methanol (6 ml) and methyl iodide (0.229 ml), and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was dissolved in ethanol (12 ml). Ammonium acetate (43 mg) was added, and the mixture was stirred at 75° C. for 2 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=95:5-90:10) and dried under reduced pressure to give the title compound (113 mg).

Provenance & Evidence