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	US05998436
Source dataset	uspto-grants-1999_12
ORD ID	ord-9f3c000f270d4b56becf7b12f6e40be7
Source note	uspto-grants-1999_12