Cesium carbonate → 4-chloro-N-(2,5-difluoro-4-(oxazol-2-yl)benzyl)-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide

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Reaction Steps

The title compound was synthesized from 4-chloro-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (90 mg, 0.30 mmol), cesium carbonate (117 mg, 0.36 mmol), and 2-(4-(bromomethyl)-2,5-difluorophenyl)oxazole (99 mg, 0.36 mmol) according to the procedure described for 4-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (Example 20) to give 4-chloro-N-(2,5-difluoro-4-(oxazol-2-yl)benzyl)-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (46 mg, 31%). 1H NMR (400 MHz, CDCl3) δ ppm 7.77 (s, 1H), 7.74 (d, J=8.56 Hz, 2H), 7.68 (dd, J=9.95, 5.67 Hz, 1H), 7.52 (dd, J=9.95, 5.67 Hz, 1H), 7.49 (d, J=8.56 Hz, 2H), 7.29 (s, 1H), 4.52 (d, J=16.00 Hz, 1H), 4.37 (d, J=16.00 Hz, 1H), 3.53-3.65 (m, 2H), 3.12 (d, J=11.08 Hz, 1H), 2.57 (d, J=1.01 Hz, 1H), 1.58-1.77 (m, 3H), 1.36-1.53 (m, 2H), 0.98-1.21 (m, 4H). Analytical HPLC R.T.=22.02 min. MS [M+H]+=497. HRMS [M+H]+ calc'd 497.1113, found 497.1100.

Provenance & Evidence