Hydrochloric Acid → N-{(S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoyl}-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

(S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid (25 mg, 0.062 mmol) is dissolved THF (0.5 mL) and CDI (22 mg, 0.14 mmol) is added into it at room temperature. The mixture is stirred for 30 min and then it is heated at 55° C. for 1 hr. After the mixture is cooled down to room temperature, Benzenesulfonamide (19 mg, 0.12 mmol) is added and after 10 min, DBU (0.018 mL, 0.12 mmol) is added. The mixture is then stirred for 16 hr at room temperature. 1 mL of 1.0 M HCl is added followed by 10 mL of water. The mixture is extracted with EtOAc (3×20 mL) and the organic layers are combined, dried and concentrated to give crude product. Purification by Preparative TLC affords 16 mg (47%) of N-{(S)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoyl}-benzenesulfonamide. LCMS (ESMS): m/z 545.32 (M+H+).

Provenance & Evidence