1,2-Dichloroethane → 4-{4-[2-(5-Tert-butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-benzo[b]thiophen-7-ylcarbamoyl]-benzenesulfonyl}-piperazine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

7-Amino-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide (0.100 g, 0.223 mmol), 4-(4-carboxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (0.160 g, 0.432 mmol), HOBT (0.060 g, 0.444 mmol) and EDC (0.080 g, 0.417 mmol) were dissolved in DMF (7.0 mL) and stirred at room temperature under an Ar atmosphere for 42 h. The reaction mixture was transferred to a separatory funnel containing water and the aqueous layer was extracted with EtOAc (3×10 mL). The combined organic extracts were washed with water, NH4Cl, brine and dried over MgSO4. The solvent was filtered and evaporated on a rotary evaporator. The resultant crude product was purified by chromatography (60% EtOAc/hexane) to give the desired 4-{4-[2-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-benzo[b]thiophen-7-ylcarbamoyl]-benzenesulfonyl}-piperazine-1-carboxylic acid tert-butyl ester (25.5 mg).

Provenance & Evidence