Dimethyl Sulfoxide → 7-(3-Aminoazetidin-1-yl)-1-(4-amino-3,5,6-trifluoropyridin-2-yl)-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 610196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 610196
CS(C)=O.Cl.Cl.[NH2:7][CH:8]1[CH2:11][NH:10][CH2:9]1.[NH2:12][C:13]1[C:18]([F:19])=[C:17]([F:20])[N:16]=[C:15]([N:21]2[C:30]3[C:25](=[CH:26][C:27]([F:33])=[C:28](F)[C:29]=3[Cl:31])[C:24](=[O:34])[C:23]([C:35]([OH:37])=[O:36])=[CH:22]2)[C:14]=1[F:38]>C(N(CC)CC)C>[NH2:7][CH:8]1[CH2:11][N:10]([C:28]2[C:29]([Cl:31])=[C:30]3[C:25]([C:24](=[O:34])[C:23]([C:35]([OH:37])=[O:36])=[CH:22][N:21]3[C:15]3[C:14]([F:38])=[C:13]([NH2:12])[C:18]([F:19])=[C:17]([F:20])[N:16]=3)=[CH:26][C:27]=2[F:33])[CH2:9]1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 13491919Azetidin-3-amine--hydrogen chloride (1/2)HCID 221212331-(4-Amino-3,5,6-trifluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Produkt 1

HCID 221211907-(3-Aminoazetidin-1-yl)-1-(4-amino-3,5,6-trifluoropyridin-2-yl)-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To 1 ml dimethylsulfoxide solution of 70 mg of 3-aminoazetidine dihydrochloride and 250 mg of triethylamine at 80° C. was added 150 mg of 1-(4-amino-3,5,6-trifluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid with stirring, and the mixture was stirred at 80° C. for 1 hour. The reaction solution was allowed to cool and decanted with diethylether. Ethanol was added to the residue to disperse the solid content, and the solid content was collected by filtration, washed with ethanol, and dried to obtain 85 mg of the title compound as a pale yellow powder.

Aufarbeitung

  1. stirringthe mixture was stirred at 80° C. for 1 hour
  2. temperatureto cool
  3. customdecanted with diethylether
  4. additionEthanol was added to the residue
  5. additionto disperse the solid content
  6. filtrationthe solid content was collected by filtration
  7. washwashed with ethanol
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d7d419c005744199b4aeb01d5c823b12
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998436

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