Sodium 2-propanethiolate → HCID 56668008, compound

Participants

Reaction Steps

To a stirred solution of phenyl N-cyano-4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidine-1-carboximidoate (20 mg, 0.035 mmol) in THF (1 mL) was added sodium 2-propanethiolate (6.8 mg, 0.07 mmol). The resulting mixture was stirred at ambient temperature for 30 minutes before evaporation of the solvent. The crude product was then purified by flash chromatography on silical gel, eluting with a gradient of 0-10% methanol in ethyl acetate to afford isopropyl N-cyano-4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidine-1-carbimidothioate as a white solid (14 mg, 72%). 1H NMR (300 MHz, CDCl3) δ 7.69 (d, J=7.5 Hz, 1H), 7.45-7.40 (m, 2H), 7.32-7.24 (m, 4H), 7.21-7.14 (m, 2H), 4.39-4.26 (m, 3H), 3.53 (br, 4H), 2.65 (s, 3H), 2.33-2.05 (m, 4H), 1.99-1.85 (m, 13H), 1.38 (d, J=6.4 Hz, 6H). HRMS m/z (M+H)+ calcd: 555.3270, obsd: 555.3274.

Provenance & Evidence