N-(1-Acryloyl-piperidin-4-yl)-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide → N-Cyclopropyl-N-{1-[3-(4-hydroxy-cyclohexylamino)-propionyl]-piperidin-4-yl}-3-trifluoromethyl-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

N-(1-Acryloyl-piperidin-4-yl)-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide (1) (125 mg, 0.31 mmol), trans-4-aminocyclohexanol (357 mg, 3.1 mmol) and ETOH (2.5 ml) were mixed together in a sealed tube and heated to 150° C. with microwave equipment for 30 min. After the reaction, the reaction mixture was evaporated in vacuum and the residue was purified by column chromatography on silica gel (CHCl3/MeOH/NH3 aq.=100/10/1) to afford the desired compound as free base, which was dissolved in AcOEt (2 ml), and treated with 4N—HCl in AcOEt (2 ml) solution. The resulting mixture was concentrated in vacuo, and dried under reduced pressure for 24 hours at 60° C. to afford the title compound 3 as a HCl-salt (colorless amorphous, 141 mg, yield 82%) LC: 100%. MS: m/z=517.88, 518.51 (M+H+).

Provenance & Evidence