Pyridine → 1-(5-Amino-2,4-difluorophenyl)-8-chloro-6-fluoro-7-(2,2,2-trifluoroethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

HRID 369299Notes

Reaction equation

[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].N1C=CC=CC=1.[NH2:13][C:14]1[C:15]([F:38])=[CH:16][C:17]([F:37])=[C:18]([N:20]2[C:29]3[C:24](=[CH:25][C:26]([F:32])=[C:27](F)[C:28]=3[Cl:30])[C:23](=[O:33])[C:22]([C:34]([OH:36])=[O:35])=[CH:21]2)[CH:19]=1>C(OCC)C>[NH2:13][C:14]1[C:15]([F:38])=[CH:16][C:17]([F:37])=[C:18]([N:20]2[C:29]3[C:24](=[CH:25][C:26]([F:32])=[C:27]([NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])[C:28]=3[Cl:30])[C:23](=[O:33])[C:22]([C:34]([OH:36])=[O:35])=[CH:21]2)[CH:19]=1

Participants

Conditions

Temperature: 40 °C

Procedure

2,2,2-Trifluoroethylamine (50 mg) and pyridine (300 ml) were added to 1-(5-amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (110 mg), and the mixture was stirred at 40° C. for 2 days. Additional 2,2,2-trifluoroethylamine (50 mg) was added, and the mixture was stirred at 40° C. for 2 days. Diethyl ether was added to the reaction mixture, followed by stirring. A supernatant liquid was removed, and solids deposited were collected by filtration and washed with ethanol to obtain the title compound (90 mg) as a colorless powder.

Workup

stirringthe mixture was stirred at 40° C. for 2 days
stirringby stirring
customA supernatant liquid was removed
filtrationsolids deposited were collected by filtration
washwashed with ethanol

Sources & evidence

ORD record: ord-5bc60a61a04546088e6433649359800b
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136823

Reaction notes

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