Dichloromethane → HCID 89692973, compound

In a 40 ml scintillation vial equipped with a magnetic stir bar and fitted with a nitrogen inlet, the 5-amino-2-chloro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid 14a (107.50 mg, 0.31 mmol) was taken up in clean, dry, reagent grade dichloromethane (5.00 ml, 77.53 mmol) and the mixture was stirred until all solids were in solution. To this stirred solution was added the N,N-diisopropylethylamine (0.16 ml, 0.92 mmol) followed by the furan-2-carbonyl chloride (0.04 ml, 0.41 mmol) and the reaction was allowed to stir at room temperature overnight. The reaction was analyzed by LCMS, which showed that mixed anhydride had formed along with the desired compound. The reaction was then concentrated under reduced pressure and taken back up in methanol and the solution was then treated with saturated NaHCO3 solution and the mixture was stirred for 2 h. The mixture was then diluted with 20 ml of water and 20 ml of dichloromethane. The layers were separated and the product was extracted from the aqueous using dichloromethane (3×10 ml). The organic phases were combined, washed with brine (1×25 ml) and dried over MgSO4. The solution was filtered under vacuum and the collected solution was then concentrated under reduced pressure. The product, 2-chloro-5-[(furan-2-carbonyl)-amino]-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid 14b (135.70 mg, 0.31 mmol), was isolated as a yellowish solid and was carried on without further purification. LCMS (m/e)=439 (M+H).