Formic Acid → 7-(5-Formyl-2,5-diazabicyclo-(2.2.1)hept-2-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 727940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 727940
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:29])[C:13]([C:26]([OH:28])=[O:27])=[CH:14][N:15]2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])=[CH:10][C:9]=1[F:30].C[C:32](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:33].C(O)=O>CN(C=O)C>[CH:32]([N:5]1[CH2:6][CH:1]2[CH2:7][CH:4]1[CH2:3][N:2]2[C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:29])[C:13]([C:26]([OH:28])=[O:27])=[CH:14][N:15]2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])=[CH:10][C:9]=1[F:30])=[O:33]

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 140148307-(2,5-Diazabicyclo(2.2.1)hept-2-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

Produkt 1

HCID 140148337-(5-Formyl-2,5-diazabicyclo-(2.2.1)hept-2-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acidAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.5 g (1.2 m Mol) 7-(2,5-diazabicyclo(2.2.1)hept-2-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid was suspended in 20 ml DMF and treated with 3 ml of the mixed anhydride of acetic and formic acid. After 90 mins. stirring at room temperature the volatiles were removed under reduced pressure. The oily residue was triturated with ether, the residue filtered and recrystallized from a mixture of 20 ml DMF and 5 ml ligroin to give 0.24 g (45.3%) of product, mp 252° C.-258° C. dec.

Aufarbeitung

  1. customwere removed under reduced pressure
  2. customThe oily residue was triturated with ether
  3. filtrationthe residue filtered
  4. customrecrystallized from a mixture of 20 ml DMF and 5 ml ligroin

Quellen und Nachweise

ORD-Eintrag
ord-fcab305469594d9f8a94ef4457f95a9b
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05045549

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