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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 562472Generated: October 31, 2026

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

https://huagongshe.com/reaction/562472

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantDiisopropylethylamineHCID 81531—
Reactant4-Chloro-6-hydrazinylpyrimidineHCID 247222—
Reactant4,4-Difluoropiperidine hydrochlorideHCID 2758351—
ReactantEthyl 2-(4-cyanotriazol-1-yl)-3-(dimethylamino)prop-2-enoateHCID 66725972—
SolventWaterHCID 962—
Product1-{2-[6-(4,4-Difluoropiperidin-1-yl)pyrimidin-4-yl]-3-oxo-2,3-dihydro-1H-pyrazol-4-yl}-1H-1,2,3-triazole-4-carbonitrileHCID 44464867—

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 325 mg (1.4 mmol) of the compound from Example 7A, 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: 34 mg (7% of theory)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08067407B2
Source datasetuspto-grants-2011_11
ORD IDord-5ce40dbdcbab4a6f9c0a890041fe03d4
Source noteuspto-grants-2011_11