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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 368450Generated: October 29, 2026

Dimethylformamide → 1-(6-Amino-3-chloro-5-fluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-methylaminoazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

https://huagongshe.com/reaction/368450

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantN-methyl-2-pyrrolidoneHCID 13387—
ReactantN-methylazetidin-3-amine dihydrochlorideHCID 22121158—
Reactant1-(6-Amino-3-chloro-5-fluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 22121179—
SolventEthanolHCID 702—
Product1-(6-Amino-3-chloro-5-fluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-methylaminoazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 2212122581.8%

Reaction Conditions

Temperature85 °C

Reaction Steps

To 300 mg of N,N-dimethylformamide were added 103 mg of 1-(6-amino-3-chloro-5-fluoropyridine-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 85 mg of 3-methylaminoazetidine dihydrochloride, and 150 mg of N-methylpyrrolidone, and the mixture was stirred at 85° C. for 30 minutes. After adding 0.3 ml of ethanol, the mixture was allowed to cool, and the precipitate was collected by filtration and washed with ethanol and diisopropylether successively to obtain 98 mg of the title compound as a colorless powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06133284
Source datasetuspto-grants-2000_10
ORD IDord-437adad03728414fb24dfa79f550715a
Source noteuspto-grants-2000_10