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

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	1-Methylpyrrolidine	HCID 8454	—
Reactant	1-(6-Amino-3,5-difluoro-2-pyridinyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid	HCID 15434901	—
Reactant	N-methylazetidin-3-amine dihydrochloride	HCID 22121158	—
Solvent	Ethanol	HCID 702	—
Product	1-(6-Amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-methylaminoazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	HCID 15486976	87.3%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To 400 mg of N,N-dimethylformamide were added 90 mg of 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 80 mg of 3-methylaminoazetidine dihydrochloride, and 160 mg of N-methylpyrrolidine, and the mixture was stirred at 90° C. for 1 hour. After adding 0.5 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 92 mg of the title compound as a colorless powder.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06156903
Source dataset	uspto-grants-2000_12
ORD ID	ord-0deb6231f4c64951b8d9a43342df83fa
Source note	uspto-grants-2000_12