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

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Reaction Steps

The title compound was synthesized from 4-chloro-N-(cis-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (119 mg, 0.38 mmol), cesium carbonate (244 mg, 0.75 mmol), and 3-(4-(bromomethyl)phenyl)-1,2,4-oxadiazole (99 mg, 0.41 mmol) according to the procedure described for 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (Example 40) to give N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(cis-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (12 mg, 7%). 1H NMR (400 MHz, CDCl3) δ ppm 8.75 (1H, s), 8.05 (2H, d, J=8.56 Hz), 7.68-7.70 (1H, m), 7.66-7.68 (1H, m), 7.47 (2H, d, J=8.56 Hz), 7.43-7.45 (1H, m), 7.41-7.43 (1H, m), 4.67 (1H, d, J=16.62 Hz), 4.44 (1H, d, J=16.62 Hz), 4.23-4.35 (1H, m), 3.60 (1H, dd, J=11.33, 8.56 Hz), 3.35 (1H, dd, J=11.46, 5.41 Hz), 1.99 (1H, br. s.), 1.38-1.81 (6H, m), 1.09-1.32 (5H, LC/MS R.T.=3.09 min; [M+H]+=476.23.

Provenance & Evidence