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

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	1-Methylpyrrolidine	HCID 8454	—
Reactant	3-Methylazetidin-3-amine dihydrochloride	HCID 14852453	—
Reactant	1-(6-Amino-3,5-difluoro-2-pyridinyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid	HCID 15434901	—
Solvent	Ethanol	HCID 702	—
Product	1-(6-Amino-3,5-difluoropyridin-2-yl)-7-(3-amino-3-methylazetidin-1-yl)-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	HCID 15486978	68.3%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To 350 mg of N,N-dimethylformamide were added 80 mg of 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 60 mg of 3-amino-3-methylazetidine dihydrochloride, and 150 mg of N-methylpyrrolidine, and the mixture was stirred at 90° C. for 40 minutes. After adding 0.5 ml of ethanol, the mixture was allowed to cool, and the precipitate was collected by filtration and washed with ethanol to obtain 64 mg of the title compound as a pale yellow powder.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06156903
Source dataset	uspto-grants-2000_12
ORD ID	ord-be3e6d583caa484fb57cd24f528e44a6
Source note	uspto-grants-2000_12