Benzoic Acid → HCID 25124529, compound

Participants

Reaction Conditions

Reaction Steps

Benzoic acid (6.1 mg, 0.050 mmol) is dissolved THF (0.50 mL) and 1,1′-carbonyl diimidazole (9.1 mg, 0.056 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, 2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid amide (10 mg, 0.025 mmol) is added and after 10 min, 1,8-diazabicyclo[5,4,0]undec-7-ene (0.007 mL, 0.050 mmol) is added. The mixture is stirred for 16 hr at room temperature. 1.0 M HCl solution (1.0 mL) is added followed by water (10 mL). 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 using 6% MeOH in EtOAc affords 11 mg (85%) of 2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethanesulfonic acid benzoylamide. LCMS (ESMS): m/z 506.25 (M+H+).

Provenance & Evidence