Dichloromethane → HCID 56832521, compound

Participants

Reaction Steps

A 100 mL round-bottomed flask was charged with 1,1,1,3,3,3-hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol (2.27 g, 6.92 mmol, published PCT patent application no. WO 2006/094842), 20 mL of CH2Cl2 and triethylamine (1.45 mL, 10.4 mmol). To this was added 2-thiophenesulfonyl chloride (1.39 mL, 7.61 mmol, Sigma-Aldrich, St. Louis, Mo.) and the mixture was stirred at room temperature for 2 h. After that time, the mixture was diluted with water (50 mL) and extracted with EtOAc (100 mL). The combined extracts were dried (MgSO4) and concentrated. This oil was purified by column chromatography (120 g silica gel, 0 to 50% EtOAc in hexanes) to give 1,1,1,3,3,3-hexafluoro-2-(4-(4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (2.35 g) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.70-7.65 (m, 1H) 7.64-7.56 (m, 3H), 7.23-7.18 (m, 1H), 7.02-6.94 (m, 2H), 3.43-3.36 (m, 4H), 3.33-3.25 (m, 4H). m/z (ESI, +ve ion) 475.0 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=0.332 μM; GK-GKRP EC50 (LC MS/MS)=0.500 μM.

Provenance & Evidence