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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2048591Generated: 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'-methoxybiphenyl-2-carbonitrile

https://huagongshe.com/reaction/2048591

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
ReactantEthyl 2-[(2'-cyano-3-methoxybiphenyl-4-yl)methyl]-3-oxohexanoateHCID 67009516—
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'-methoxybiphenyl-2-carbonitrileHCID 6700888286%

Reaction Steps

A solution of N-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-5-amine (0.53 g), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.071 mL) and ethyl 2-[(2′-cyano-3-methoxybiphenyl-4-yl)methyl]-3-oxohexanoate (1.81 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 (1.1 g, 83%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08592431B2
Source datasetuspto-grants-2013_11
ORD IDord-39c0a63fbc7843bf9dd56c685e67b086
Source noteuspto-grants-2013_11