Cesium carbonate → 4-chloro-N-(trans-2-(hydroxymethyl)cycloheptyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide

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Reaction Steps

The title compound was synthesized from 4-chloro-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (80 mg, 0.25 mmol), cesium carbonate (164 mg, 0.50 mmol), and 2-(4-(bromomethyl)phenyl)oxazole (72 mg, 0.30 mmol) according to the procedure described for 4-Chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (Example 40) to give 4-chloro-N-(trans-2-(hydroxymethyl)cycloheptyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide (104 mg, 87%). 1H NMR (400 MHz, CDCl3) δ ppm 7.99 (2H, d, J=8.31 Hz), 7.73-7.75 (1H, m), 7.71-7.73 (1H, m), 7.69 (1H, s), 7.51 (1H, s), 7.48 (2H, s), 7.44-7.47 (1H, m), 7.21 (1H, s), 4.69 (1H, d, J=15.86 Hz), 3.99 (1H, d, J=15.61 Hz), 3.74-3.85 (1H, m), 3.67 (1H, dd, J=11.58, 4.28 Hz), 3.28 (1H, dd, J=11.58, 2.27 Hz), 2.27 (1H, br. s.), 1.42-1.65 (6H, m), 1.12-1.39 (5H, m). LC/MS R.T.=2.25 min; [M+H]+=475.22. HRMS [M+H]+ calc'd 475.1458, found 475.1459.

Provenance & Evidence