Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(4-(Bromomethyl)-3-fluorophenyl)-1,3-oxazole | HCID 58201748 | — |
| Reactant | N-((1R,2R)-2-acetylcyclohexyl)-4-chlorobenzenesulfonamide | HCID 59497774 | — |
| Reactant | 4-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide | HCID 59497780 | — |
| Product | HCID 59497804 | HCID 59497804 | 70.2% |
Reaction Steps
The title compound was synthesized from N-((1R,2R)-2-acetylcyclohexyl)-4-chlorobenzenesulfonamide as a clear oil (550 mg, 1.74 mmol), cesium carbonate (700 mg, 2.15 mmol), and 2-(4-(bromomethyl)-3-fluorophenyl)oxazole (513 mg, 2.00 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 N-((1R,2R)-2-acetylcyclohexyl)-4-chloro-N-(2-fluoro-4-(oxazol-2-yl)benzyl)benzenesulfonamide as a clear oil (600 mg, 70% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.66-7.78 (m, 4H), 7.63 (dd, J=10.83, 1.51 Hz, 1H), 7.51 (t, J=7.93 Hz, 1H), 7.36-7.43 (m, 2H), 7.21 (s, 1H), 4.41 (s, 2H), 3.93 (t, J=10.07 Hz, 1H), 2.74 (1, J=9.57 Hz, 1H), 1.79-1.91 (m, 4H), 1.58-1.71 (m, 3H), 1.43-1.55 (m, 1H), 1.10-1.22 (m, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07977362B2 |
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| Source dataset | uspto-grants-2011_07 |
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| ORD ID | ord-af4973f2e5df4bf9b83594da1f8104a1 |
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| Source note | uspto-grants-2011_07 |
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