Dimethylformamide → 7-(3-Aminoazetidin-1-yl)-1-(6-amino-3,5-difluoropyridin-2-yl)-5,6,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 610278Notes

Reaction equation

CN(C)C=O.[NH2:6][C:7]1[N:12]=[C:11]([N:13]2[C:22]3[C:17](=[C:18]([F:26])[C:19]([F:25])=[C:20](F)[C:21]=3[F:23])[C:16](=[O:27])[C:15]([C:28]([OH:30])=[O:29])=[CH:14]2)[C:10]([F:31])=[CH:9][C:8]=1[F:32].Cl.Cl.[NH2:35][CH:36]1[CH2:39][NH:38][CH2:37]1.CN1CCCC1>C(O)C>[NH2:35][CH:36]1[CH2:39][N:38]([C:20]2[C:21]([F:23])=[C:22]3[C:17]([C:16](=[O:27])[C:15]([C:28]([OH:30])=[O:29])=[CH:14][N:13]3[C:11]3[C:10]([F:31])=[CH:9][C:8]([F:32])=[C:7]([NH2:6])[N:12]=3)=[C:18]([F:26])[C:19]=2[F:25])[CH2:37]1

Participants

Conditions

Temperature: 90 °C

Procedure

To 300 mg of N,N-dimethylformamide were added 100 mg of 1-(6-amino-3,5-difluoropyridin-2-yl)-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 70 mg of 3-aminoazetidine dihydrochloride, and 150 mg of N-methylpyrrolidine, and the mixture was stirred at 90° C. for 30 minutes. After adding 0.3 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 50 mg of the title compound as a pale yellow powder.

Workup

temperatureto cool
filtrationthe precipitate was collected by filtration
washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record: ord-d8fcc9107d3d4875b1acdd0a35d0b8e5
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998436

Reaction notes

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