Methanesulfonic Acid → 1-Cyclopropyl-8-difluoromethoxy-6-fluoro-7-(3-methylpiperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid methanesulfonic acid salt

HRID 1648663Notes

Reaction equation

HRID 1648663 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:30])=[C:16]([N:23]4[CH2:28][CH2:27][NH:26][CH:25]([CH3:29])[CH2:24]4)[C:17]=3[O:19][CH:20]([F:22])[F:21])[C:12](=[O:31])[C:11]([C:32]([OH:34])=[O:33])=[CH:10]2)[CH2:8][CH2:7]1>CO>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:30])=[C:16]([N:23]4[CH2:28][CH2:27][NH:26][CH:25]([CH3:29])[CH2:24]4)[C:17]=3[O:19][CH:20]([F:22])[F:21])[C:12](=[O:31])[C:11]([C:32]([OH:34])=[O:33])=[CH:10]2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 150237881-Cyclopropyl-8-difluoromethoxy-6-fluoro-7-(3-methylpiperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 867452961-Cyclopropyl-8-difluoromethoxy-6-fluoro-7-(3-methylpiperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid methanesulfonic acid saltYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.093 g (0.00097 moles) of methanesulfonic acid was added to a suspension of 0.40 g of 1-cyclopropyl-8-difluoromethoxy-6-fluoro-7-(3-methylpiperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (prepared as described in Example 1) in 50 ml of methanol to obtain a transparent solution. This was concentrated by evaporation under reduced pressure, and the residue was washed with ethanol, to give 0.47 g of the title compound (methanesulfonic acid salt) as a colorless powder, melting at 289°-292° C. (with decomposition).

Workup

  1. customto obtain a transparent solution
  2. concentrationThis was concentrated by evaporation under reduced pressure
  3. washthe residue was washed with ethanol

Sources & evidence

ORD record
ord-99ce3fa1fbeb4a139041a16e1c865321
Source dataset
uspto-grants-1995_07
Patent number
US05436367

Reaction notes

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