Dimethylformamide → 7-(3-Aminoazetidin-1-yl)-8-chloro-6-fluoro-1-(3,5-difluoro-6-isopropylaminopyridin-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1274765Notes

Reaction equation

CN(C)C=O.[Cl:6][C:7]1[C:8](F)=[C:9]([F:33])[CH:10]=[C:11]2[C:16]=1[N:15]([C:17]1[C:22]([F:23])=[CH:21][C:20]([F:24])=[C:19]([NH:25][CH:26]([CH3:28])[CH3:27])[N:18]=1)[CH:14]=[C:13]([C:29]([OH:31])=[O:30])[C:12]2=[O:32].Cl.Cl.[NH2:37][CH:38]1[CH2:41][NH:40][CH2:39]1.CN1CCCC1>C(O)C>[NH2:37][CH:38]1[CH2:41][N:40]([C:8]2[C:7]([Cl:6])=[C:16]3[C:11]([C:12](=[O:32])[C:13]([C:29]([OH:31])=[O:30])=[CH:14][N:15]3[C:17]3[C:22]([F:23])=[CH:21][C:20]([F:24])=[C:19]([NH:25][CH:26]([CH3:27])[CH3:28])[N:18]=3)=[CH:10][C:9]=2[F:33])[CH2:39]1

Participants

Conditions

Temperature: 80 °C

Procedure

To 160 mg of N,N-dimethylformamide were added 55 mg of 8-chloro-6,7-difluoro-1-(3,5-difluoro-6-isopropylamino-pyridine-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 35 mg of 3-aminoazetidine dihydrochloride, and 120 mg of N-methylpyrrolidine, and the mixture was stirred at 80° C. for 30 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 and diisopropylether successively to obtain 51 mg of the title compound as a colorless powder.

Workup

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

Sources & evidence

ORD record: ord-fbb9c4dbb0104e268cd7c0f8c45adee5
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156903

Reaction notes

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