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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1753824Generated: October 28, 2026

p-Toluenesulfonic acid → 4-(1H-Imidazol-1-yl)-2-(6-piperidin-1-ylpyrimidin-4-yl)-1,2-dihydro-3H-pyrazol-3-one

https://huagongshe.com/reaction/1753824

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-Toluenesulfonic acidHCID 6101—
Reactant4-Hydrazinyl-6-(piperidin-1-yl)pyrimidineHCID 44140305—
ReactantEthyl 3-(N,N-dimethylamino)-2-(1H-imidazol-1-yl)acrylateHCID 66726242—
SolventEthyl AcetateHCID 8857—
Product4-(1H-Imidazol-1-yl)-2-(6-piperidin-1-ylpyrimidin-4-yl)-1,2-dihydro-3H-pyrazol-3-oneHCID 59603655—

Reaction Steps

5.5 g (26.3 mmol) of the compound from Example 42A and 6.1 g (31.5 mmol) of the compound from Example 8A are dissolved in 55 ml ethyl acetate and 1.2 g (10.5 mmol) p-toluenesulfonic acid are added. The mixture is heated to the reflux and is stirred at this temperature for 16 h. After cooling to RT, the precipitate is filtered off and washed with ethyl acetate. The solid is dissolved in 50 ml water and the solution is adjusted to pH 7 with 1 N hydrochloric acid. The precipitate is filtered off, washed with water and diisopropyl ether and finally dried over phosphorus pentoxide.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09168249B2
Source datasetuspto-grants-2015_10
ORD IDord-ff1426cd92e84ca8883edc7c09cecee7
Source noteuspto-grants-2015_10