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1-Methylpyrrolidine → 5-Amino-7-(3-aminoazetidin-1-yl)-1-(6-amino-3,5-difluoropyridin-2-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 610282
Notes
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Reaction equation

HRID 610282 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:27])[C:5]([C:24]([OH:26])=[O:25])=[CH:6][N:7]2[C:15]1[C:20]([F:21])=[CH:19][C:18]([F:22])=[C:17]([NH2:23])[N:16]=1.Cl.Cl.[NH2:30][CH:31]1[CH2:34][NH:33][CH2:32]1.CN1CCCC1>CN(C)C=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:33]2[CH2:34][CH:31]([NH2:30])[CH2:32]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:27])[C:5]([C:24]([OH:26])=[O:25])=[CH:6][N:7]2[C:15]1[C:20]([F:21])=[CH:19][C:18]([F:22])=[C:17]([NH2:23])[N:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 84541-MethylpyrrolidineHCID 13491919Azetidin-3-amine--hydrogen chloride (1/2)HCID 221212615-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 221212765-Amino-7-(3-aminoazetidin-1-yl)-1-(6-amino-3,5-difluoropyridin-2-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 45.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 210 mg of N,N-dimethylformamide were added 50 mg of 5-amino-1-(6-amino-3,5-difluoropyridin-2-yl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 40 mg of 3-aminoazetidine dihydrochloride, and 150 mg of N-methylpyrrolidine, and the mixture was stirred at 90° C. for 1 hour, and concentrated under reduced pressure. The procedure of adding 2 ml of diisopropylether to the residue, stirring and decanting was repeated twice. 2 ml of ethanol and 40 mg of N-methylpyrrolidine were added to the residue, and the mixture was allowed to stand overnight, and the precipitate was collected by filtration and washed with ethanol and diisopropylether successively to obtain 26 mg of the title compound as a pale yellow powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe procedure of adding 2 ml of diisopropylether to the residue
  3. stirringstirring
  4. customdecanting
  5. addition2 ml of ethanol and 40 mg of N-methylpyrrolidine were added to the residue
  6. waitto stand overnight
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-850689a697ac4547898182cd61b14e22
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05998436

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes