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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1412550Generated: October 26, 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}-2'-methylbiphenyl-2-carbonitrile

https://huagongshe.com/reaction/1412550

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
ReactantN-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-5-amineHCID 67009993—
ReactantEthyl 2-[(2'-cyano-2-methylbiphenyl-4-yl)methyl]-3-oxohexanoateHCID 67010208—
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}-2'-methylbiphenyl-2-carbonitrileHCID 6700865574%

Reaction Steps

A solution of N-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-5-amine (0.59 g), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.080 mL) and ethyl 2-[(2′-cyano-2-methylbiphenyl-4-yl)methyl]-3-oxohexanoate (1.5 g) in diethylaniline (3 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 (1.0 g, 74%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08921379B2
Source datasetuspto-grants-2014_12
ORD IDord-4bafaefef671442998f6235663109cc2
Source noteuspto-grants-2014_12