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

HRID 368404Notes

Reaction equation

HRID 368404 reaction equation
CN(C)C=O.[NH2:6][C:7]1[N:12]=[C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([F:25])=[C:20](F)[C:21]=3[Cl:23])[C:16](=[O:26])[C:15]([C:27]([OH:29])=[O:28])=[CH:14]2)[C:10]([F:30])=[CH:9][C:8]=1[F:31].Cl.Cl.[NH2:34][CH:35]1[CH2:38][NH:37][CH2:36]1.CN1CCCC1>C(O)C>[NH2:34][CH:35]1[CH2:38][N:37]([C:20]2[C:21]([Cl:23])=[C:22]3[C:17]([C:16](=[O:26])[C:15]([C:27]([OH:29])=[O:28])=[CH:14][N:13]3[C:11]3[C:10]([F:30])=[CH:9][C:8]([F:31])=[C:7]([NH2:6])[N:12]=3)=[CH:18][C:19]=2[F:25])[CH2:36]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 84541-MethylpyrrolidineHCID 13491919Azetidin-3-amine--hydrogen chloride (1/2)HCID 154349011-(6-Amino-3,5-difluoro-2-pyridinyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 5103787-(3-Aminoazetidin-1-yl)-1-(6-amino-3,5-difluoro-2-pyridyl)-8-chloro-6-fluoro-4-oxo-quinoline-3-carboxylic acidYield 75.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To 350 mg of N,N-dimethylformamide were added 100 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-aminoazetidine dihydrochloride and 150 mg of N-methylpyrrolidine, and the mixture was stirred at 90° C. for 1 hour. After adding 1 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 86 mg of the title compound as a colorless powder.

Workup

  1. temperatureto cool
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-cfa7728b894a4f4787d27bb951d4bb28
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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