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Triethylamine → 1-(5-Amino-2,4-difluorophenyl)-8-chloro-6-fluoro-7-(3,3,3-trifluoro-2-hydroxypropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

HRID 369309
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 369309
[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1.[NH2:27][CH2:28][CH:29]([OH:34])[C:30]([F:33])([F:32])[F:31].C(N(CC)CC)C>N1C=CC=CC=1>[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([NH:27][CH2:28][CH:29]([OH:34])[C:30]([F:33])([F:32])[F:31])[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 4189653-Amino-1,1,1-trifluoropropan-2-olHCID 108619991-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Produkt 1

HCID 232847741-(5-Amino-2,4-difluorophenyl)-8-chloro-6-fluoro-7-(3,3,3-trifluoro-2-hydroxypropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic AcidAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1-(5-Amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (150 mg), 1-amino-3,3,3-trifluoro-2-propanol (120 mg) and triethylamine (120 mg) were added to pyridine (400 mg), and the mixture was stirred for 20 hours at room temperature and for 6 hours at 60° C. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (3 ml) to the residue and then concentrating the mixture under reduced pressure was conducted twice repeatedly. Concentrated hydrochloric acid (150 mg) was added to the residue, and the mixture was concentrated under reduced pressure. Ethanol (2 ml) was added to the resultant residue, and deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (153 mg) as a colorless powder.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationA process of adding ethanol (3 ml) to the residue and then concentrating the mixture under reduced pressure
  3. additionConcentrated hydrochloric acid (150 mg) was added to the residue
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionEthanol (2 ml) was added to the resultant residue, and deposits
  6. filtrationwere collected by filtration
  7. washwashed with ethanol and diisopropyl ether in that order

Quellen und Nachweise

ORD-Eintrag
ord-f56d9ac37ede47889fd58883d4e6dc97
Quelldatensatz
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06136823

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