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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2062755Generated: November 1, 2026

Ethyl Acetate → 4'-{[4-(1,4-Dioxaspiro[4.5]dec-8-yl)-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}-3'-fluorobiphenyl-2-carbonitrile

https://huagongshe.com/reaction/2062755

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
ReactantEthyl 2-[(2'-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 57460949—
ReactantN-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-5-amineHCID 67009993—
SolventWaterHCID 962—
SolventN,N-DiethylanilineHCID 7061—
Product4'-{[4-(1,4-Dioxaspiro[4.5]dec-8-yl)-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}-3'-fluorobiphenyl-2-carbonitrileHCID 6700895577.1%

Reaction Steps

A solution of N-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-5-amine (2.2 g), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.30 mL) and ethyl 2-[(2′-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxohexanoate (7.4 g) in diethylaniline (10 mL) was stirred at 180° C. for 2 hr. The mixture was allowed to cool, ethyl acetate and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (4.0 g, 75%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08283353B2
Source datasetuspto-grants-2012_10
ORD IDord-120047dce4c84294b9569315e811750b
Source noteuspto-grants-2012_10