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

Reaktionsgleichung

Reaktionsgleichung von HRID 25175
[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]

Komponenten

6

Edukt 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

Produkt 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 acidAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f1b6525d2c034223888dbf7e1495eaa4
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858625B1

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