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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 405837Generated: October 25, 2026

Chloroacetic anhydride → N-(5-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

https://huagongshe.com/reaction/405837

Reaction equation

Participants

RoleNameHCIDCharge
ReactantChloroacetic anhydrideHCID 10946—
ReactantN-(5-(N'-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamideHCID 86677441—
SolventWaterHCID 962—
SolventN-methyl-2-pyrrolidoneHCID 13387—
ProductN-(5-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamideHCID 86677445—

Reaction Conditions

Temperature110 °C

Reaction Steps

A mixture of N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide 9 (500 mg, 1.62 mmol) and 2-chloroacetic anhydride (553 mg, 3.23 mmol) in anhydrous 1-methyl-2-pyrrolidinone (10 mL) was heated in the microwave at 110° C. for 12 minutes. The crude was diluted with water and extracted with ethyl acetate. The organic was washed with water/brine mixture and dried over anhydrous sodium sulfate. The crude product was purified by silica chromatography. MS m/z 368.08 (M+1)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08754071B2
Source datasetuspto-grants-2014_06
ORD IDord-3fa0a85c1d5141e5a6e1c73da4977fbc
Source noteuspto-grants-2014_06