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

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Reaction Steps

The title compound was synthesized from 4-chloro-N-(trans-2-hydroxymethylcyclopentyl)benzenesulfonamide (145 mg, 0.5 mmol), cesium carbonate (326 mg, 1.0 mmol), and 2-(4-(bromomethyl)phenyl)oxazole (143 mg, 0.6 mmol) according to the procedure described for 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (Example 2) to give 4-chloro-N-(trans-2-(hydroxymethyl)cyclopentyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide (178 mg, 80%). 1H NMR (400 MHz, CDCl3) δ ppm 7.99 (2H, d, J=8.31 Hz), 7.66-7.78 (3H, m), 7.43-7.50 (4H, m), 7.22 (1H, s), 4.70 (1H, d, J=16.12 Hz), 4.15 (1H, d, J=16.12 Hz), 3.97-4.08 (1H, m), 3.57 (1H, dd, J=11.58, 4.28 Hz), 3.42 (1H, dd, J=11.46, 3.65 Hz), 1.34-1.71 (8H, m). LC/MS R.T.=2.14 min; [M+H]+=447.12. HRMS [M+H]+ calc'd 447.1145, found 447.1139.

Provenance & Evidence