Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2039494Generated: November 1, 2026

Trifluoroacetic acid → 1-{2-[6-(4,4-Difluoropiperidin-1-yl)pyrimidin-4-yl]-3-oxo-2,3-dihydro-1H-pyrazol-4-yl}-1H-imidazole-4-carbonitrile

https://huagongshe.com/reaction/2039494

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantDiisopropylethylamineHCID 81531—
Reactant4-Chloro-6-hydrazinylpyrimidineHCID 247222—
Reactant4,4-Difluoropiperidine hydrochlorideHCID 2758351—
ReactantEthyl 3-(N,N-dimethylamino)-2-(4-cyano-1H-imidazol-1-yl)acrylateHCID 66726020—
SolventWaterHCID 962—
Product1-{2-[6-(4,4-Difluoropiperidin-1-yl)pyrimidin-4-yl]-3-oxo-2,3-dihydro-1H-pyrazol-4-yl}-1H-imidazole-4-carbonitrileHCID 44464866—

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 200 mg (1.4 mmol) of the compound from Example 11A, 262 mg (1.7 mmol) of 4,4-difluoropiperidine hydrochloride and 289 μl (215 mg, 1.7 mmol) of N-ethyl-N-(propan-2-yl)propane-2-amine in 3 ml of water is stirred at 100° C. for 16 h. Following the addition of 53 μl (79 mg, 0.7 mmol) of trifluoroacetic acid and 324 mg (1.4 mmol) of the compound from Example 6A, the reaction mixture is stirred at 100° C. for 16 h. The precipitated solid is filtered off and washed first with water and then with diethyl ether. The product is dried under reduced pressure. Yield: 111 mg (21% of theory)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08580778B2
Source datasetuspto-grants-2013_11
ORD IDord-06152b95302448718a7ff5feda8bdf43
Source noteuspto-grants-2013_11