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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 872984Generated: October 30, 2026

Water → 4-(5-chloro-4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)picolinamide

https://huagongshe.com/reaction/872984

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant4-Chloropyridine-2-carboxamideHCID 303543—
ReactantPotassium tert-butoxideHCID 23665647—
ReactantN-(2-chloro-5-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideHCID 90033637—
SolventDimethylformamideHCID 6228—
Product4-(5-chloro-4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)picolinamideHCID 7305326560.5%

Reaction Conditions

Temperature120 °C

Reaction Steps

To a suspension of N-(2-chloro-5-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (751.6 mg, 2 mmol) and t-BuOK (224.4 mg, 2 mmol) in DMF (4 mL) and was added 4-chloropicolinamide (313.2 mg, 2 mmol). The reaction was warmed up to 120° C. and stirred for 15 hours. After the mixture cooling to rt, H2O (40 mL) was added and the resulted mixture was stirred at rt overnight. Filtered and the filter cake was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=50/1) to give the title compound as a light yellow solid (290 mg, 60.5%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08975282B2
Source datasetuspto-grants-2015_03
ORD IDord-f620c4a3c78a4b37b193eb358e42507c
Source noteuspto-grants-2015_03