2-Methylpiperazine → 5-Amino-1-cyclopropyl-8-difluoromethoxy-6-fluoro-7-(3-methylpiperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1648664Notes

Reaction equation

HRID 1648664 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[NH2:8][C:9]1[C:18]([F:19])=[C:17](F)[C:16]([O:21][CH:22]([F:24])[F:23])=[C:15]2[C:10]=1[C:11](=[O:31])[C:12]([C:28]([OH:30])=[O:29])=[CH:13][N:14]2[CH:25]1[CH2:27][CH2:26]1>N1C=CC=CC=1>[NH2:8][C:9]1[C:18]([F:19])=[C:17]([N:6]2[CH2:5][CH2:4][NH:3][CH:2]([CH3:1])[CH2:7]2)[C:16]([O:21][CH:22]([F:23])[F:24])=[C:15]2[C:10]=1[C:11](=[O:31])[C:12]([C:28]([OH:30])=[O:29])=[CH:13][N:14]2[CH:25]1[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 660572-MethylpiperazineHCID 150238455-Amino-1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 150238035-Amino-1-cyclopropyl-8-difluoromethoxy-6-fluoro-7-(3-methylpiperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 64.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.30 g (0.013 moles) of 2-methylpiperazine was added to a solution of 0.90 g (0.0026 moles) of 5-amino-1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (prepared as described in Preparation 11) in 8 ml of pyridine, and the mixture was stirred at 105°-110° C. for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure. Water was added to the residue, and the resulting mixture was neutralized (to about pH 7) by the addition of acetic acid; the mixture was then extracted with chloroform. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated by evaporation under reduced pressure. The resulting residue was washed with ethanol to give 0.72 g of 5-amino-1-cyclopropyl-8-difluoromethoxy-6-fluoro-7-(3-methylpiperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid as a yellow powder, melting at 283°-286° C.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. additionWater was added to the residue
  3. additionby the addition of acetic acid
  4. extractionthe mixture was then extracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. washThe resulting residue was washed with ethanol

Sources & evidence

ORD record
ord-524f6c6f5692436e9600284426ec4770
Source dataset
uspto-grants-1995_07
Patent number
US05436367

Reaction notes

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