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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 46276Generated: October 25, 2026

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

https://huagongshe.com/reaction/46276

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantDi-tert-butyl (chloromethyl) phosphateHCID 11701630—
Reactant4-[4-Chloro-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]-3-cyano-N-1,3-thiazol-2-ylbenzenesulfonamideHCID 59436599—
SolventDimethylformamideHCID 6228—
Productditert-butyl [(2Z)-2-[4-[4-chloro-2-(2-methylpyrazol-3-yl)phenoxy]-3-cyanophenyl]sulfonylimino-1,3-thiazol-3-yl]methyl phosphateHCID 5943648784.9%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08541588B2
Source datasetuspto-grants-2013_09
ORD IDord-eb9168d4d0454f33aaae5d15c6791e6a
Source noteuspto-grants-2013_09