2-Methylpiperazine → Gatifloxacin

HRID 492107

Reaktionsgleichung

[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11](F)[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:22][CH:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1>CS(C)=O>[CH3:22][CH:23]1[NH:24][CH2:25][CH2:26][N:27]([C:11]2[C:12]([O:14][CH3:15])=[C:13]3[N:4]([CH:1]4[CH2:3][CH2:2]4)[CH:5]=[C:6]([C:19]([OH:21])=[O:20])[C:7](=[O:18])[C:8]3=[CH:9][C:10]=2[F:17])[CH2:28]1

Komponenten

Reaktionsbedingungen

Temperatur: 55 °C

Versuchsvorschrift

Twenty grams of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid and 14.2 g (2.1 eq) of 2-methyl piperazine were suspended in DMSO (400 mL) under a blanket of nitrogen. The mixture was heated to 55° C. during 24 hours. Subsequently, the mixture was heated to 70° C. and half of the amount of DMSO was distilled-off at reduced pressure (1-5 mm Hg). At the end of the distillation, dimethylcarbonate (200 mL) was added, the reaction mixture was cooled to 5° C. and held at this temperature overnight. The mixture was then filtered under vacuum. The compound was then dried under vacuum to obtain 20.22 g after assay (76% yield) of gatifloxacin.

Aufarbeitung

temperatureSubsequently, the mixture was heated to 70° C.
distillationAt the end of the distillation, dimethylcarbonate (200 mL)
additionwas added
temperaturethe reaction mixture was cooled to 5° C.
customheld at this temperature overnight
filtrationThe mixture was then filtered under vacuum
customThe compound was then dried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-17082d6fb6454a5da892a613c2306ed1
Quelldatensatz: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07531656B2

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