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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 25175Generated: October 25, 2026

Diisopropyl Ether → 1-(6-Amino-3,5-difluoropyridin-2-yl)-8-bromo-7-(3-ethylaminoazetidin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

https://huagongshe.com/reaction/25175

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropyl EtherHCID 7914—
Reactant1-MethylpyrrolidineHCID 8454—
ReactantN-ethylazetidin-3-amineHCID 10336591—
Reactant1-(6-Amino-3,5-difluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 15486977—
SolventDimethyl SulfoxideHCID 679—
Product1-(6-Amino-3,5-difluoropyridin-2-yl)-8-bromo-7-(3-ethylaminoazetidin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 995804977.6%

Reaction Conditions

Temperature40 °C

Reaction Steps

3-Ethylaminoazetidine (700 mg), 1-(6-amino-3,5-difluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1.5 g), N-methyl-pyrrolidine (2.0 g)and dimethylsulfoxide (4.5 g) were combined, and the mixture was heated under stirring at 40° C. for 24 hours. After the mixture was allowed to cool down, isopropyl ether (10 mL) was added, the mixture was stirred, and a clear layer at the top of the mixture was removed. The same procedure was repeated once more, and the residue was concentrated under reduced pressure. Ethanol (5 mL) was added, and the mixture was heated under stirring at 70° C. for 30 minutes. The precipitated solid was collected by filtration. The title compound (1.38 g) was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06858625B1
Source datasetuspto-grants-2005_02
ORD IDord-f1b6525d2c034223888dbf7e1495eaa4
Source noteuspto-grants-2005_02