HCID 14651194, compound → HCID 14651163, compound

HRID 232689Notes

Reaction equation

HRID 232689 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]([CH3:24])=[C:22]3[C:17]([C:18](=[O:31])[C:19]([C:28]([OH:30])=[O:29])=[CH:20][N:21]3[CH:25]3[CH2:27][CH2:26]3)=[C:16]([CH3:32])[C:15]=2[F:33])[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[N:11]1([C:14]2[C:23]([CH3:24])=[C:22]3[C:17]([C:18](=[O:31])[C:19]([C:28]([OH:30])=[O:29])=[CH:20][N:21]3[CH:25]3[CH2:26][CH2:27]3)=[C:16]([CH3:32])[C:15]=2[F:33])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 14651194HCID 14651194, compound

Product 1

HCID 14651163HCID 14651163, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 7-(4-benzyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-5,8-dimethyl-1, 4-dihydro-4-oxo-quinoline-3-carboxylic acid (150 mg) in ethanol (20 ml) is added 10% Pd-C (50 mg) and the catalytic reduction is carried out at 70° C. under atomospheric pressure. After filtering off the 10% Pd-C, the filtrate is concentrated. The residue is recrystallized from dimethylformamide to give 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-5,8-dimethyl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid (64 mg), m.p. 185°-187° C., as pale yellow needles.

Workup

  1. customis carried out at 70° C. under atomospheric pressure
  2. filtrationAfter filtering off the 10% Pd-C
  3. concentrationthe filtrate is concentrated
  4. customThe residue is recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-e6ce9ff3a63948ce917b4079f972df4f
Source dataset
uspto-grants-1997_01
Patent number
US05591744

Reaction notes

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