Dichloromethane → N-(3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-yl)-N-propylsulfamide

Participants

Reaction Steps

A mixture of the product from Step 6 (100 mg, 0.27 mmol), triethylamine (110 mg, 1.1 mmol) and propylsulfamoyl chloride (170 mg, 1.1 mmol) in DCM (5 ml) was stirred at ambient temperature for 18 hrs. The reaction mixture was diluted with water (20 ml) and extracted with ethyl acetate (3×20 ml). The organic extracts were washed with brine (50 ml), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate: hexane (1:4) to afford N-(3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-yl)-N-propylsulfamide (98 mg, 74%). δH (400 MHz, CDCl3) 0.98 (3H, t, J 7.5), 1.42-1.48 (1H, m), 1.54-1.62 (4H, m), 1.82-1.90 (2H, m), 2.38-2.62 (3H, m), 2.68-2.76 (2H, m), 2.98-3.08 (3H, m), 3.72-3.77 (1H, m), 3.82 (2H, s), 4.13-4.18 (1H, m), 4.33 (1H, d, J 9.0), 6.48 (1H, s), 6.64 (1H, d, J 16.5), 7.12-7.18 (2H, m), 7.37-7.43 (2H, m), 7.45 (1H, d, J 16.5).

Provenance & Evidence