Acetonitrile → Balofloxacin dihydrate

HRID 254867노트

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HRID 254867 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 6918202Balofloxacin dihydrate수율 276.2%

시약·촉매·용매 1

HCID 8471Triethylamine용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5e7f069fb3ff4a8f812d9ea94c25e9bf
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875722B2

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