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

HRID 1725545Notes

Reaction equation

HRID 1725545 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-fe70117417d8446b864d13c0c5052126
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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