8-Aminoquinoline → 5-Acetyl-6-(3-chlorophenyl)-2-ethyl-4-(quinolin-8-ylamino)pyridazin-3(2H)-one

HRID 1725545

Reaktionsgleichung

Reaktionsgleichung von HRID 1725545
[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)=[N:8][N:7]([CH2:17][CH3:18])[C:6](=[O:19])[C:5]=1[N+:20]([O-])=O)(=[O:3])[CH3:2].N[C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:33]=1[N:32]=[CH:31][CH:30]=[CH:29]2>C(O)C>[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)=[N:8][N:7]([CH2:17][CH3:18])[C:6](=[O:19])[C:5]=1[NH:20][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:33]=1[N:32]=[CH:31][CH:30]=[CH:29]2)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 113598-AminoquinolineHCID 105198325-acetyl-2-ethyl-4-nitro-6-(3-chlorophenyl)pyridazin-3(2H)-one

Produkt 1

HCID 684861585-Acetyl-6-(3-chlorophenyl)-2-ethyl-4-(quinolin-8-ylamino)pyridazin-3(2H)-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 100 mg (0.311 mmol) of 5-acetyl-2-ethyl-4-nitro-6-(3-chlorophenyl)pyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417) in ethanol (4 mL), 8-aminoquinoline (67 mg, 0.467 mmol) was added. The resulting mixture was stirred at room temperature for two hours. The solvent was evaporated and the residue purified by column chromatography (silica gel, hexane/ethyl acetate 2:1) to yield the title compound (65 mg, 50% yield).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography (silica gel, hexane/ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-fe70117417d8446b864d13c0c5052126
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491722B2

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