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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1955002Generated: October 31, 2026

Pyridine → 8-[2-(4-Chlorobutyrylamino)-6-methylbenzylamino]-2,3-dimethylimidazo[1,2-a]pyridine

https://huagongshe.com/reaction/1955002

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyridineHCID 1049—
Reactant4-Chlorobutyryl chlorideHCID 78370—
ReactantPotassium BicarbonateHCID 516893—
Reactant8-(2-Amino-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridineHCID 10989626—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
Product8-[2-(4-Chlorobutyrylamino)-6-methylbenzylamino]-2,3-dimethylimidazo[1,2-a]pyridineHCID 2329416586.1%

Reaction Conditions

Temperature10 °C

Reaction Steps

0.88 ml (7.85 mmol) of 4-chlorobutyryl chloride is added dropwise at 0-5° C. with stirring to a solution of 2.2 g (7.85 mmol) of 8-(2-amino-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine and 0.63 ml (7.85 mmol) of pyridine in 30 ml of dichloromethane and the mixture is stirred for a further 2 h at 0-20° C. It is treated with water and potassium hydrogen carbonate to pH 7, the mixture is extracted with shaking, and the organic layer is dried with magnesium sulfate and concentrated in vacuo. The residue is recrystallized from toluene and petroleum ether (50/70° C.). 2.6 g (86%) of the title compound are obtained. M.p. 138-140° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06124313
Source datasetuspto-grants-2000_09
ORD IDord-a7a7bf1430f74ce68ea4d7fb3651938b
Source noteuspto-grants-2000_09