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Acetonitrile → 7-[(7S)-7-Amino-7-methylspiro[2.4]hept-5-yl]-1,4-dihydro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-4-oxo-3-quinolinecarboxylic acid dihydrate

HRID 254866
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HRID 254866 반응식
[C:1](#N)C.[F:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:16][CH3:17])[C:14]=1F)[N:11]([C@@H:18]1[CH2:20][C@@H:19]1[F:21])[CH:10]=[C:9]([C:22]([OH:24])=[O:23])[C:8]2=[O:25].Cl.Cl.[CH3:28][C@:29]1([NH2:36])[C:33]2([CH2:35][CH2:34]2)[CH2:32]N[CH2:30]1>C(N(CC)CC)C>[OH2:16].[OH2:16].[NH2:36][C@:29]1([CH3:28])[C:33]2([CH2:35][CH2:34]2)[CH2:32][CH:1]([C:14]2[C:13]([O:16][CH3:17])=[C:12]3[C:7]([C:8](=[O:25])[C:9]([C:22]([OH:24])=[O:23])=[CH:10][N:11]3[C@@H:18]3[CH2:20][C@@H:19]3[F:21])=[CH:6][C:5]=2[F:4])[CH2:30]1
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참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 120946186,7-difluoro-1,4-dihydro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-4-oxo-3-quinolinecarboxylic acidHCID 66700184(S)-7-Methyl-5-azaspiro[2.4]heptan-7-amine dihydrochloride

생성물 1

HCID 667002067-[(7S)-7-Amino-7-methylspiro[2.4]hept-5-yl]-1,4-dihydro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-4-oxo-3-quinolinecarboxylic acid dihydrate수율 93%

시약·촉매·용매 1

HCID 8471Triethylamine용매2회

실험 절차

An acetonitrile solution (24 mL) containing 6,7-difluoro-1,4-dihydro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-4-oxo-3-quinolinecarboxylic acid (3 g), (7S)-7-methyl-5-azaspiro[2.4]heptan-7-amine dihydrochloride (3 g), triethylamine (1.34 mL), and boron trifluoride-tetrahydrofuran complex (2.68 g) was stirred at room temperature for 30 minutes. Boron trifluoride-tetrahydrofuran complex (0.27 g) was further added to the solution, followed by stirring for one hour at the same temperature. Triethylamine (5.37 mL) was further added to the reaction mixture, followed by stirring at room temperature for 5 hours. The solvent was evaporated under reduced pressure, and methanol (30 mL) was added to the residue. The mixture was refluxed for 2 hours, and the solvent was evaporated. 90% Hydrated methanol was added to the residue, and the pH of the product was adjusted to 8 by use of 5N aqueous sodium hydroxide. The thus-obtained mixture was stirred at 60° C. for 40 minutes, and the pH of the product was adjusted to 7 by use of 5N aqueous sodium hydroxide solution, followed by stirring at 5° C. for 16 hours. The thus-produced crystals were recovered through filtration and dried, to thereby yield 4.23 g of the title compound (yield: 93%). Spectral data of this compound coincided with those obtained in Example 1.

후처리

  1. additionBoron trifluoride-tetrahydrofuran complex (0.27 g) was further added to the solution
  2. stirringby stirring for one hour at the same temperature
  3. stirringby stirring at room temperature for 5 hours
  4. customThe solvent was evaporated under reduced pressure, and methanol (30 mL)
  5. additionwas added to the residue
  6. temperatureThe mixture was refluxed for 2 hours
  7. customthe solvent was evaporated
  8. addition90% Hydrated methanol was added to the residue
  9. stirringThe thus-obtained mixture was stirred at 60° C. for 40 minutes
  10. stirringby stirring at 5° C. for 16 hours
  11. filtrationThe thus-produced crystals were recovered through filtration
  12. customdried

출처 및 근거

ORD 기록
ord-d9d6ece7c11e4564a82d73f461866358
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07875722B2

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