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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 870449Generated: November 1, 2026

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(2-chloro-5-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

https://huagongshe.com/reaction/870449

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
ReactantHOAtHCID 181649—
ReactantAntipyric acidHCID 246564—
Reactant4-Amino-5-chloro-2-fluorophenolHCID 11240656—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductN-(2-chloro-5-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideHCID 9003363753.2%

Reaction Conditions

Temperature80 °C

Reaction Steps

To a suspension of 4-amino-5-chloro-2-fluorophenol (0.97 g, 6 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carb oxylic acid (1.42 g, 6.12 mmol) in DMF (20 mL) was added EDCI (0.38 mg, 7.2 mmol) and HOAT (0.16 g, 1.2 mmol). The mixture was allowed to warm up to 80° C. and stirred for 24 hours. Then H2O (200 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at 0° C. for 2 hours, then filtered to give the title compound as a light brown solid (1.2 g, 53.2%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08969388B1
Source datasetuspto-grants-2015_03
ORD IDord-082c2cfe38cd4ebba04c371abd807db4
Source noteuspto-grants-2015_03