1-Hydroxybenzotriazole → HCID 66755035, compound

Participants

Reaction Steps

A mixture of [6-cyano-3-(4-methoxy-benzenesulfonyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-phenyl-acetic acid XIIIc (200 mg, 0.43 mmol), 1-hydroxybenzotriazole (88 mg, 0.65 mmol) and PS-carbodiimide resin (Argonaut; 1.18 mmol/g; 439 mg, 0.52 mmol) in CH2Cl2 (5 mL) was agitated for 10 min at room temperature. Then, 1-benzyl-4-(S)-pyrrolidin-3-yl-piperazine (166 mg, 0.47 mmol) was added and the reaction mixture was agitated at room temperature overnight. To this mixture MP-carbonate resin (Argonaut; 2.69 mmol/g; 481 mg, 1.29 mmol) was added and the reaction mixture was agitated for another 2 hours, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using 5% MeOH in CH2Cl2 as eluent to afford 3-{2-[(S)-3-(4-benzyl-piperazin-1-yl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-1-(4-methoxy-benzenesulfonyl)-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbonitrile (135 mg, 45%) as a white solid.

Provenance & Evidence