HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-chloro-N-(trans-2-hydroxymethylcyclohexyl)benzenesulfonamide | HCID 59497770 | — |
| Reactant | 4-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide | HCID 59497780 | — |
| Reactant | 3-(4-(Bromomethyl)phenyl)-1,2,4-oxadiazole | HCID 66670019 | — |
| Product | N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide | HCID 59497773 | 48.1% |
Reaction Steps
The title compound was synthesized from 4-chloro-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (28 mg, 0.09 mmol), cesium carbonate (36 mg, 0.11 mmol), and 3-(4-(bromomethyl)phenyl)-1,2,4-oxadiazole (26 mg, 0.11 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-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (20 mg, 48%). MS [M+H]+=462 HRMS [M+H]+ calc'd 462.1254, found 462.1255. Chiral LC: R.T.=16.21 min., 98.0% ee.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07977362B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-97f8a74e1ac642d7b534031e05d24125 |
| Source note | uspto-grants-2011_07 |