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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2048561Generated: October 31, 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/2048561

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 numberUS08592431B2
Source datasetuspto-grants-2013_11
ORD IDord-e028147059e142dab61ceb733a857f8a
Source noteuspto-grants-2013_11