Cesium carbonate → N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide

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Reaction Steps

A suspension of 4-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (300 mg, 1.0 mmol), cesium carbonate (390 mg, 1.2 mmol), and 3-(4-(bromomethyl)phenyl)-1,2,4-oxadiazole (280 mg, 1.2 mmol) in dimethylformamide (5 mL) was stirred for 2 h. The reaction was concentrated and purified by flash chromatography on a 40 g silica gel column using a gradient of 0 to 80% ethyl acetate in hexane, then by preparative HPLC to give N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (70 mg, 15%). 1H NMR (400 MHz, MeOD) δ ppm 9.23 (s, 1H), 8.00 (d, J=8.30 Hz, 2H), 7.75 (d, J=8.81 Hz, 2H), 7.54 (d, J=8.00 Hz, 2H), 7.51 (d, J=8.60 Hz, 2H), 4.55 (d, J=15.61 Hz, 1H), 4.36 (d, J=15.86 Hz, 1H), 3.52 (br. s., 1H), 3.31-3.38 (m, 1H), 3.14 (dd, J=11.08, 7.30 Hz, 1H), 1.87 (d, J=12.34 Hz, 1H), 1.53-1.75 (m, 2H), 1.30-1.53 (m, 3H), 0.98-1.22 (m, 3H). LC/MS R.T.=2.72 min; [M+H]+=462. HRMS [M+H]+ calc'd 462.1254, found 462.1241.

Provenance & Evidence