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Diisopropyl Ether → 1-(6-Amino-3,5-difluoropyridin-2-yl)-8-bromo-7-(3-ethylaminoazetidin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 25175
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인쇄 미리보기

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HRID 25175 반응식
[CH2:1]([NH:3][CH:4]1[CH2:7][NH:6][CH2:5]1)[CH3:2].[NH2:8][C:9]1[N:14]=[C:13]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:27])=[C:22](F)[C:23]=3[Br:25])[C:18](=[O:28])[C:17]([C:29]([OH:31])=[O:30])=[CH:16]2)[C:12]([F:32])=[CH:11][C:10]=1[F:33].CN1CCCC1.C(OC(C)C)(C)C>CS(C)=O>[NH2:8][C:9]1[N:14]=[C:13]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:27])=[C:22]([N:6]4[CH2:7][CH:4]([NH:3][CH2:1][CH3:2])[CH2:5]4)[C:23]=3[Br:25])[C:18](=[O:28])[C:17]([C:29]([OH:31])=[O:30])=[CH:16]2)[C:12]([F:32])=[CH:11][C:10]=1[F:33]
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참가 물질

6

반응물 4

HCID 7914Diisopropyl EtherHCID 84541-MethylpyrrolidineHCID 10336591N-ethylazetidin-3-amineHCID 154869771-(6-Amino-3,5-difluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

생성물 1

HCID 99580491-(6-Amino-3,5-difluoropyridin-2-yl)-8-bromo-7-(3-ethylaminoazetidin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid수율 77.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
40 °C

실험 절차

3-Ethylaminoazetidine (700 mg), 1-(6-amino-3,5-difluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1.5 g), N-methyl-pyrrolidine (2.0 g)and dimethylsulfoxide (4.5 g) were combined, and the mixture was heated under stirring at 40° C. for 24 hours. After the mixture was allowed to cool down, isopropyl ether (10 mL) was added, the mixture was stirred, and a clear layer at the top of the mixture was removed. The same procedure was repeated once more, and the residue was concentrated under reduced pressure. Ethanol (5 mL) was added, and the mixture was heated under stirring at 70° C. for 30 minutes. The precipitated solid was collected by filtration. The title compound (1.38 g) was obtained.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto cool down
  3. stirringthe mixture was stirred
  4. customa clear layer at the top of the mixture was removed
  5. concentrationthe residue was concentrated under reduced pressure
  6. additionEthanol (5 mL) was added
  7. temperaturethe mixture was heated
  8. stirringunder stirring at 70° C. for 30 minutes
  9. filtrationThe precipitated solid was collected by filtration

출처 및 근거

ORD 기록
ord-f1b6525d2c034223888dbf7e1495eaa4
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06858625B1

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