1-Cyclopropyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → Gatifloxacin

HRID 2249255

Reaction equation

HRID 2249255 reaction equation
[CH3:1][O-:2].[Na+].[Na].[CH:5]1([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:26])=[C:15]([N:19]4[CH2:24][CH2:23][NH:22][CH:21]([CH3:25])[CH2:20]4)[C:16]=3F)[C:11](=[O:27])[C:10]([C:28]([OH:30])=[O:29])=[CH:9]2)[CH2:7][CH2:6]1>CO>[CH:5]1([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:26])=[C:15]([N:19]4[CH2:24][CH2:23][NH:22][CH:21]([CH3:25])[CH2:20]4)[C:16]=3[O:2][CH3:1])[C:11](=[O:27])[C:10]([C:28]([OH:30])=[O:29])=[CH:9]2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 4620611-Cyclopropyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 5379Gatifloxacin

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide prepared from sodium (0.4 g) and absolute methanol (20 ml) was added 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid (1.12 g), and, the mixture in sealed tube was stirred for 70.5 hours at 140° to 150° C. and then concentrated. The residue was dissolved in small amount of water, the resulting solution was adjusted to pH 7 with acetic acid and concentrated. The resulting residue was purified by silica gel column chromatography eluting with chloroform-methanol-concentrated aqueous ammonia (20:6:1) and recrystallized from methanol to give the title compound (0.33 g) as pale yellow prisms, mp 162°- C.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in small amount of water
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel column chromatography
  5. washeluting with chloroform-methanol-concentrated aqueous ammonia (20:6:1)
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-3142b9d8840c434aac5135dd617232a5
Source dataset
uspto-grants-1991_08
Patent number
US05043450

Linked notes

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