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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1692317Generated: October 26, 2026

Potassium Carbonate → tert-butyl {[4-(4-chloro-2-{1-[1-(diphenylmethyl)azetidin-3-yl]-1H-pyrazol-5-yl}phenoxy)-3-cyanophenyl]sulfonyl}1,3-thiazol-4-ylcarbamate

https://huagongshe.com/reaction/1692317

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
ReactantAmmonium ChlorideHCID 25517—
Reactanttert-Butyl [(3-cyano-4-fluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamateHCID 59436569—
Reactant2-[2-(1-Benzhydryl-azetidin-3-yl)-2H-pyrazol-3-yl]-4-chloro-phenolHCID 136063630—
SolventDimethyl SulfoxideHCID 679—
Producttert-butyl {[4-(4-chloro-2-{1-[1-(diphenylmethyl)azetidin-3-yl]-1H-pyrazol-5-yl}phenoxy)-3-cyanophenyl]sulfonyl}1,3-thiazol-4-ylcarbamateHCID 59436484—

Reaction Steps

4-chloro-2-{1-[1-(diphenylmethyl)azetidin-3-yl]-1H-pyrazol-5-yl}phenol, (Preparation 689, 75 mg, 0.18 mmol), tert-butyl [(3-cyano-4-fluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate (Preparation 250, 69 mg, 0.18 mmol), potassium carbonate (62 mg, 0.45 mmol) and dimethyl sulphoxide (4 ml) were combined and stirred at room temperature under nitrogen for 4 hours. Saturated aqueous ammonium chloride solution (20 ml) was added and the mixture extracted with ethyl acetate (1×20 ml). The organic layer was separated and back-washed with saturated aqueous sodium chloride solution (2×20 ml). The organic layer was separated, dried over sodium sulphate, filtered and evaporated to give an oil. The oil was purified using an ISCO® Companion (4 g. silica gel, gradient from dichloromethane to dichloromethane:methanol 98:2). The appropriate fractions were combined and solvents removed in vacuo to give the title compound as a glass. Yield 33 mg. 24%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08153814B2
Source datasetuspto-grants-2012_04
ORD IDord-0ff3f97bb1264e03a94183818773bcbb
Source noteuspto-grants-2012_04