Methanesulfonic Acid → Garenoxacin mesylate

HRID 1018535Notes

Reaction equation

HRID 1018535 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:18]4[CH:19]=[C:20]5[C:24](=[CH:25][CH:26]=4)[C@@H:23]([CH3:27])[NH:22][CH2:21]5)[C:12]=3[O:14][CH:15]([F:17])[F:16])[C:7](=[O:28])[C:6]([C:29]([OH:31])=[O:30])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:32][S:33]([OH:36])(=[O:35])=[O:34]>C(O)C>[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:18]4[CH:19]=[C:20]5[C:24](=[CH:25][CH:26]=4)[C@@H:23]([CH3:27])[NH:22][CH2:21]5)[C:12]=3[O:14][CH:15]([F:17])[F:16])[C:7](=[O:28])[C:6]([C:29]([OH:31])=[O:30])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 124093Garenoxacin

Product 1

HCID 124094Garenoxacin mesylateYield 81.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

In 4 ml of ethanol is suspended 0.2 g of (R)-1-cyclopropyl-8-difluoromethoxy-7-(1-methyl-2,3-dihydro-1H-5-isoindolyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid and then the suspension is warmed to 70° C., after which 45 mg of methanesulfonic acid is added to the warmed suspension to form a uniform solution. Subsequently, the solution is stirred at the same temperature for 1 hour and then cooled to room temperature, after which the crystals deposited are collected by filtration to obtain 0.20 g of (R)-1-cyclopropyl-8-difluoromethoxy-7-(1-methyl-2,3-dihydro-1H-5-isoindolyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid methanesulfonate.

Workup

  1. customto form a uniform solution
  2. temperaturecooled to room temperature
  3. filtrationafter which the crystals deposited are collected by filtration

Sources & evidence

ORD record
ord-435e9de6f905416e8f67df9a3d377c95
Source dataset
uspto-grants-2002_11
Patent number
US06482835B2

Reaction notes

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