Dabco → 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid

HRID 1382215Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1382215
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[OH:20][CH:21]1[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24][CH2:23][CH:22]1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.N12CCN(CC1)CC2>CS(C)=O>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:33]4[CH2:34][CH2:35][N:30]([CH:22]5[CH:21]([OH:20])[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24][CH2:23]5)[CH2:31][CH2:32]4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Komponenten

5

Edukt 3

HCID 9237DabcoHCID 483180Fluoroquinolonic acidHCID 212744861-(6-Hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-piperazine

Produkt 1

HCID 138507991-Cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acidAusbeute 10,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

2.8 g (10 mmol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are heated at 140° in 30 ml of dimethyl sulphoxide with 2.5 g (11 mmol) of 1-(6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-piperazine and 2.25 g (20 mmol) of 1,4-diazabicyclo[2.2.2]octane for 4 hours, the reaction mixture is concentrated, the resulting oil is diluted with 20 ml of methanol and the pH is brought to 5 with 2N hydrochloric acid. The precipitate which has separated out is recrystallized from glycol monomethyl ether/methanol. 0.5 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid of melting point 255°-262° (with decomposition) is obtained, and is dissolved in 10 ml of 2N hydrochloric acid, with warming, to split off the protective group. After the solution has been left to stand at room temperature for 1 hour, 0.3 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(1,3,4-trihydroxy-2-butyl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid of melting point 262°-268° (with decomposition) has precipitated.

Aufarbeitung

  1. concentrationthe reaction mixture is concentrated
  2. additionthe resulting oil is diluted with 20 ml of methanol
  3. customThe precipitate which has separated out
  4. customis recrystallized from glycol monomethyl ether/methanol

Quellen und Nachweise

ORD-Eintrag
ord-7a4dccf680bd4060b9ba03215390077d
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04806539

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