Water → HCID 86690646, compound

Participants

Reaction Steps

To a solution of N-[[4-(4-acetylpiperazin-1-yl)phenyl]methyl]-1-phenyl-methanesulfonamide (100 mg, 0.25 mmol) in N,N-dimethylacetamide (3 mL) was added sodium hydride (60% in mineral oil) (11.3 mg, 0.28 mmol) and stirred at ambient temperature for 30 minutes. 2,2,2-Trifluoroethyl trifluoromethanesulfonate (72 mg, 0.31 mmol) was then added and stirred at ambient temperature for 16 hours. Water was added and the reaction was partitioned between water and dichloromethane. The dichloromethane layer was isolated with a phase separator cartridge and concentrated and purified by preparative reverse phase HPLC to yield 47 mg of N-(4-(4-acetylpiperazin-1-yl)benzyl)-1-phenyl-N-(2,2,2-trifluoroethyl)methanesulfonamide. 1H NMR (400 MHz, DMSO) δ 7.47-7.32 (m, 5H), 7.21 (d, J=8.5 Hz, 2H), 6.95 (d, J=8.5 Hz, 2H), 4.52 (s, 2H), 4.27 (s, 2H), 3.83 (q, J=9.3 Hz, 2H), 3.62-3.51 (m, 4H), 3.22-3.13 (m, 2H), 3.13-3.03 (m, 2H), 2.03 (s, 3H); LCMS (m/z) ES+ 470.1 [M+1]+.

Provenance & Evidence