Diisopropylethylamine → HCID 17940104, compound

Participants

Reaction Steps

A solution of 1-[4-methoxy-3-(4-methylpiperazin-1-yl)benzenesulfonyl]-7-trifluoromethyl-1,2,3,4-tetrahydroquinoline (E8) (70 mg, 0.15 mmol) and 1-chloro-ethyl chloroformate (0.08 ml, 0.75 mmol) in 1,2-dichloroethane (2 ml) was heated under reflux for 18 h, and then was cooled to ambient temperature. N,N-Diisopropylethylamine (0.05 ml, 0.26 mmol) was added and the resulting solution was heated under reflux for 2 h. The solvent was removed, the residue was dissolved in methanol (4 ml), and the reaction was heated under reflux for 18 h. The solvent was partially removed, dichloromethane (20 ml) was added, and the solution was washed with saturated aqueous sodium hydrogen carbonate (10 ml), dried (MgSO4), and then evaporated. The residue was purified by column chromatography on silica gel eluting with a methanol-dichloromethane gradient to afford the sulfonamide derivative as a yellowish oil. The oil was dissolved in acetone (0.5 ml) and 1M solution of hydrogen chloride in diethyl ether (0.1 ml) was added. The solution was evaporated, and the residue was coevaporated with dry benzene (3×2 ml) to give the title compound (E25) as a cream solid (38 mg, 52%).

Provenance & Evidence