Hydrochloric Acid → N-{3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]hexanoyl}-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid (56 mg, 0.14 mmol) is dissolved in dry THF (1.0 mL) and 1,1′-carbonyl diimidazole (50 mg, 0.29 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 (46 mg, 0.29 mmol) is added and after 10 min, 1,8-diazabicyclo[5,4,0]undec-7-ene (0.044 mL, 0.29 mmol) is added. The mixture is stirred for 3 hr at room temperature. Then 1.0 M HCl (3 mL) is added followed by water (30 mL). The mixture is extracted with EtOAc (3×50 mL) and the organic layers are combined, dried and concentrated to give crude product. Purification by preparative TLC using 2% MeOH in CH2Cl2 affords 63 mg (84%) of N-{3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]hexanoyl}-benzenesulfonamide. LCMS (ESMS): m/z 548.11 (M+H+).

Provenance & Evidence