Piperazine → 1-(6-Amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-4-oxo-7-piperazino-1,4-dihydroquinoline-3-carboxylic acid

HRID 610178Notes

Reaction equation

HRID 610178 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].[NH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>C(O)C>[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]([N:32]4[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]4)[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]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 6228DimethylformamideHCID 154349011-(6-Amino-3,5-difluoro-2-pyridinyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 154869791-(6-Amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-4-oxo-7-piperazino-1,4-dihydroquinoline-3-carboxylic acidYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To 170 mg of N,N-dimethylformamide were added 50 mg of 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 50 mg of piperazine, and the mixture was stirred at 90° C. for 1 hour. After adding about 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 33 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-ff2e7d05b64646089c5bdd86307143aa
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

Loading…