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Ethyl 1-(6-amino-3,5-difluoropyridin-2-yl)-5-benzylamino-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate → Ethyl 5-amino-1-(6-amino-3,5-difluoropyridin-2-yl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1274772
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1274772
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:17]3[C:12](=[C:13]([NH:21]CC4C=CC=CC=4)[C:14]([F:20])=[C:15]([F:19])[C:16]=3[F:18])[C:11](=[O:29])[C:10]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:9]2)[C:5]([F:35])=[CH:4][C:3]=1[F:36]>[Pd].C(O)(=O)C>[NH2:21][C:13]1[C:14]([F:20])=[C:15]([F:19])[C:16]([F:18])=[C:17]2[C:12]=1[C:11](=[O:29])[C:10]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:9][N:8]2[C:6]1[C:5]([F:35])=[CH:4][C:3]([F:36])=[C:2]([NH2:1])[N:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 22121167Ethyl 1-(6-amino-3,5-difluoropyridin-2-yl)-5-benzylamino-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Produkt 1

HCID 22121240Ethyl 5-amino-1-(6-amino-3,5-difluoropyridin-2-yl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To 5 ml of acetic acid was added 260 mg of ethyl 1-(6-amino-3,5-difluoropyridine-2-yl)-5-benzylamino-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate together with 50 mg of 10% palladium on carbon, and the mixture was hydrogenated at room temperature for 4 hours. The catalyst was separated by filtration, and the solvent and the like were distilled off under reduced pressure. The procedure of adding 10 ml of ethanol to the residue and concentrating under reduced pressure was repeated twice. The precipitate was dispersed in ethanol, collected by filtration, and washed with ethanol and diisopropylether successively to obtain 160 mg of the title compound as a pale yellow powder.

Aufarbeitung

  1. customThe catalyst was separated by filtration
  2. distillationthe solvent and the like were distilled off under reduced pressure
  3. additionThe procedure of adding 10 ml of ethanol to the residue
  4. concentrationconcentrating under reduced pressure
  5. additionThe precipitate was dispersed in ethanol
  6. filtrationcollected by filtration
  7. washwashed with ethanol and diisopropylether successively

Quellen und Nachweise

ORD-Eintrag
ord-697fe0c09ca44da88f65f974e0b3591b
Quelldatensatz
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06156903

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