Sodium hydride → HCID 86721886, compound

Participants

Reaction Steps

A solution of 4-(4-acetyl-piperazin-1-yl)-N-isobutyl-benzenesulfonamide (100 mg, 0.295 mmol) in DMA (2 mL) was treated with NaH (60% dispersion in mineral oil, 18 mg, 0.443 mmol) and stirred at room temperature for 30 minutes. 2-(Trifluoromethyl)benzyl bromide (141 mg, 0.590 mmol) was added and the mixture heated at 90° C. for 1 hour. The cooled mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (0-100% EtOAc in DCM) gave the title compound (110 mg, 75%). 1H NMR (400 MHz, DMSO) δ 7.81 (d, J=7.9 Hz, 1H), 7.69-7.71 (m, 4H), 7.50 (t, J=7.6 Hz, 1H), 7.08 (d, J=8.8 Hz, 2H), 4.36 (s, 2H), 3.59 (d, J=5.26 Hz, 4H), 3.38 (dd, J=26.2, 5.0 Hz, 4H), 2.86 (d, J=7.2 Hz, 2H), 2.05 (s, 3H), 1.36 (t, J=6.7 Hz, 1H), 0.70 (d, J=6.6 Hz, 6H). LCMS (m/z Method B) ES+ 498.1 [M+1]+.

Provenance & Evidence