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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 624779Generated: October 30, 2026

p-Toluenesulfonic acid → HCID 178518488, compound

https://huagongshe.com/reaction/624779

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-Toluenesulfonic acidHCID 6101—
Reactant3-ChloroanilineHCID 7932—
ReactantDichloromethane methanolHCID 21226129—
ReactantHCID 178518479HCID 178518479—
SolventN-methyl-2-pyrrolidoneHCID 13387—
ProductHCID 178518488HCID 178518488—

Reaction Conditions

Temperature180 °C

Reaction Steps

To 5-((5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)thiazolidine-2,4-dione (20 mg, 0.06 mmol) in NMP was added 3-chloroaniline (38 μL, 0.36 mmol) and few granules p-toluenesulfonic acid. The reaction was heated in microwave at 180° C. for 1.5 hours. Mixture was filtered and prepared by HPLC then preparative TLC (1% methanol/dichloromethane) to yield 5-((5-(3-chlorophenylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)thiazolidine-2,4-dione as a yellow solid. LCMS (M+1=427)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09303033B2
Source datasetuspto-grants-2016_04
ORD IDord-0e8e82db66f448769a398fec76a62458
Source noteuspto-grants-2016_04