2-Methylpiperazine → rac-1-Ethyl-6-fluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinoline-carboxylic acid monosodium salt

HRID 373324

Reaktionsgleichung

Reaktionsgleichung von HRID 373324
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].[CH3:19][CH:20]1[CH2:25][NH:24][CH2:23][CH2:22][NH:21]1.C(C(CCCC)C([O-])=O)C.[Na+:36]>C(OC(=O)C)C.C(Cl)(Cl)Cl>[Na+:36].[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([N:24]3[CH2:23][CH2:22][NH:21][CH:20]([CH3:19])[CH2:25]3)[CH:11]=2)[C:6](=[O:17])[C:7]([C:14]([O-:16])=[O:15])=[CH:8]1)[CH3:13]

Komponenten

6

Edukt 3

HCID 660572-MethylpiperazineHCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 23672331Sodium 2-ethylhexanoate

Produkt 1

HCID 67896247rac-1-Ethyl-6-fluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinoline-carboxylic acid monosodium saltAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

A mixture of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid [J. Med. Chem., 23, 1358 (1980)] (0.52 g, 2 mmol) and 2-methylpiperazine (0.8 g, 8 mmol) was heated at 175° for 5 hours. The residue was dissolved in ethylacetate (10 mL) and chloroform (10 mL), and a solution of sodium-2-ethyl- hexanoate (0.33 g, 2 mmol) in ethyl acetate (20 mL) was added. The mixture was stirred for 30 minutes and the precipitate was collected. The crude product was purified by preparative liquid chromatography (C-18 reverse phase, gradient 0-40% acetonitrile in water) to give a pale yellow lyophilized solid (0.5 g, 75% yield).

Aufarbeitung

  1. temperaturewas heated at 175° for 5 hours
  2. customthe precipitate was collected
  3. customThe crude product was purified by preparative liquid chromatography (C-18 reverse phase, gradient 0-40% acetonitrile in water)

Quellen und Nachweise

ORD-Eintrag
ord-f139f0669db54306a99a6acbf3f14bfb
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05162523

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