Hydrochloric Acid → HCID 25128173, compound

Participants

Reaction Conditions

Reaction Steps

3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-4-methoxy-butyric acid (30 mg, 0.074 mmol) is dissolved THF (0.70 mL) and CDI (27 mg, 0.17 mmol) is added into it at room temperature. The mixture is heated at 55° C. for 1 hr. After the mixture is cooled down to room temperature, 1-Methyl-1H-imidazole-4-sulfonic acid amide (24 mg, 0.15 mmol) is added and after 10 min, DBU (0.022 mL, 0.15 mmol) is added. The mixture is stirred for 16 hr at room temperature. 2.0 mL of 1.0 M HCl is added followed by 20 mL of water. The mixture is extracted with EtOAc (3×25 mL) and the organic layers are combined, dried and concentrated to give crude product. Purification by flash column chromatography affords 17 mg (41%) of 1-Methyl-1H-imidazole-4-sulfonic acid {3-[3-(1,4-dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-4-methoxy-butyryl}-amide. LCMS (ESMS): m/z 551.25 (M+H+).

Provenance & Evidence