Cesium carbonate → HCID 59497783, compound

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Reaction Steps

The title compound was synthesized from 4-chloro-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (100 mg, 0.33 mmol), cesium carbonate (129 mg, 0.40 mmol), and 2-(4-(bromomethyl)-3-fluorophenyl)oxazole (101 mg, 0.40 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-fluoro-4-(oxazol-2-yl)benzyl)-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (22 mg, 14%). 1H NMR (400 MHz, CDCl3) δ ppm 7.63-7.86 (m, 6H), 7.44-7.51 (m, 2H), 7.24 (s, 1H), 4.60 (d, J=15.61 Hz, 1H), 4.38 (d, J=15.00 Hz, 1H), 3.63 (ddd, J=11.83, 4.78, 3.02 Hz, 2H), 3.00-3.11 (m, 1H), 2.57 (br. s., 1H), 1.55-1.70 (m, 3H), 1.43-1.54 (m, 2H), 0.95-1.19 (m, 4H). Analytical HPLC R.T.=23.89 min. MS [M+H]+=479. HRMS [M+H]+ calc'd 479.1208, found 479.1219. Chiral LC: R.T.=9.98 min., >98% ee.

Provenance & Evidence