Diisopropylethylamine → HCID 76284186, compound

Participants

Reaction Steps

A solution of 4-[(4-fluoro-phenyl)-isobutyl-sulfamoyl]-benzoic acid (100 mg, 0.285 mmol), 4-amino-1-methanesulfonyl piperidine (66 mg, 0.370 mmol) and DIPEA (146 μL, 0.855 mmol) in DMF (2 mL) was treated with HATU (162 mg, 0.428 mmol) and stirred at room temperature for 18 hours. The mixture was diluted with EtOAc, washed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine, dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (0-50% EtOAc in DCM) and triturating with Et2O gave the title compound (124 mg, 85%). 1H NMR (400 MHz, DMSO) δ 8.60 (d, J=7.6 Hz, 1H), 8.00 (d, J=8.3 Hz, 2H), 7.63 (d, J=8.3 Hz, 2H), 7.20 (t, J=8.7 Hz, 2H), 7.11 (dd, J=8.8, 5.0 Hz, 2H), 3.93-3.95 (m, 1H), 3.58 (d, J=11.8 Hz, 2H), 2.88 (s, 5H), 1.93 (s, 1H), 1.90 (s, 2H), 1.58-1.61 (m, 2H), 1.42-1.44 (m, 1H), 0.85 (d, J=6.6 Hz, 6H). LCMS (m/z, Method B) ES+ 511.8 [M+1]+.

Provenance & Evidence