Acetonitrile → Balofloxacin dihydrate

HRID 254867Notes

Reaction equation

HRID 254867 reaction equation
C(#N)C.[CH:4]1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([F:20])=[C:14](F)[C:15]=3[O:17][CH3:18])[C:10](=[O:21])[C:9]([C:22]([OH:24])=[O:23])=[CH:8]2)[CH2:6][CH2:5]1.Cl.Cl.[CH3:27][NH:28][CH:29]1[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]1>C(N(CC)CC)C>[OH2:17].[OH2:17].[CH:4]1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([F:20])=[C:14]([N:31]4[CH2:32][CH2:33][CH2:34][CH:29]([NH:28][CH3:27])[CH2:30]4)[C:15]=3[O:17][CH3:18])[C:10](=[O:21])[C:9]([C:22]([OH:24])=[O:23])=[CH:8]2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acidHCID 248201743-(Methylamino)piperidine Dihydrochloride

Product 1

HCID 6918202Balofloxacin dihydrateYield 276.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

An acetonitrile solution (30 mL) containing 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (3 g), 3-methylaminopiperidine dihydrochloride (2.1 g), triethylamine (1.43 mL), and boron trifluoride-tetrahydrofuran complex (2.84 g) was stirred at room temperature for 2 hours. Triethylamine (5.71 mL) was further added to the reaction mixture, followed by stirring at room temperature for 24 hours. The solvent was evaporated under reduced pressure, and methanol (30 mL) was added to the residue. The mixture was refluxed for 6 hours, and the solvent was evaporated under reduced pressure. 80% Hydrated methanol (30 mL) was added to the residue, and the pH of the product was adjusted to 8 by use of 5N aqueous sodium hydroxide solution, followed by stirring at room temperature for 16 hours. The thus-produced crystals were recovered through filtration and dried, to thereby yield 3.98 g of the title compound (yield: 92%).

Workup

  1. stirringby stirring at room temperature for 24 hours
  2. customThe solvent was evaporated under reduced pressure, and methanol (30 mL)
  3. additionwas added to the residue
  4. temperatureThe mixture was refluxed for 6 hours
  5. customthe solvent was evaporated under reduced pressure
  6. addition80% Hydrated methanol (30 mL) was added to the residue
  7. stirringby stirring at room temperature for 16 hours
  8. filtrationThe thus-produced crystals were recovered through filtration
  9. customdried

Sources & evidence

ORD record
ord-5e7f069fb3ff4a8f812d9ea94c25e9bf
Source dataset
uspto-grants-2011_01
Patent number
US07875722B2

Reaction notes

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