HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → ditert-butyl [(2Z)-2-[4-[4-chloro-2-(2-methylpyrazol-3-yl)phenoxy]-3-cyanophenyl]sulfonylimino-1,3-thiazol-3-yl]methyl phosphate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Di-tert-butyl (chloromethyl) phosphate | HCID 11701630 | — |
| Reactant | 4-[4-Chloro-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]-3-cyano-N-1,3-thiazol-2-ylbenzenesulfonamide | HCID 59436599 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | ditert-butyl [(2Z)-2-[4-[4-chloro-2-(2-methylpyrazol-3-yl)phenoxy]-3-cyanophenyl]sulfonylimino-1,3-thiazol-3-yl]methyl phosphate | HCID 59436487 | 84.9% |
Reaction Steps
4-[4-Chloro-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]-3-cyano-N-1,3-thiazol-2-ylbenzenesulfonamide, (Example 170, 200 mg, 0.000424 mol), di-tert-butyl chloromethyl phosphate (J. Med. Chem. 51 (2008) p 1111-1114, supplimentary data) (160 mg, 0.000619 mol) and cesium carbonate (420 mg, 0.00129 mol) were stirred in dimethylformamide (2 mL) at 60° C. for 18 hours. The mixture was cooled then partitioned between tert-butylmethyl ether (80 mL) and water (40 mL), the organic layer was dried over anhydrous sodium sulphate, filtered and the solvent removed in vacuo to give the title compound as a pale yellow gum, (250 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08541588B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-eb9168d4d0454f33aaae5d15c6791e6a |
| Source note | uspto-grants-2013_09 |