8-Quinolinamine, 6-bromo- → 5-Acetyl-4-[(6-bromoquinolin-8-yl)amino]-2-ethyl-6-phenylpyridazin-3(2H)-one

HRID 1725541

Reaction equation

HRID 1725541 reaction equation
[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[N+:19]([O-])=O)(=[O:3])[CH3:2].N[C:23]1[CH:24]=[C:25]([Br:33])[CH:26]=[C:27]2[C:32]=1[N:31]=[CH:30][CH:29]=[CH:28]2>C(O)C>[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[NH:19][C:23]1[CH:24]=[C:25]([Br:33])[CH:26]=[C:27]2[C:32]=1[N:31]=[CH:30][CH:29]=[CH:28]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 936378-Quinolinamine, 6-bromo-HCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 684856495-Acetyl-4-[(6-bromoquinolin-8-yl)amino]-2-ethyl-6-phenylpyridazin-3(2H)-oneYield 85.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 80 mg (0.279 mmol) of 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417) in ethanol (4 mL), 8-amino-6-bromoquinoline (93 mg, 0.417 mmol) was added. The resulting mixture was stirred at room temperature or one day. The solvent was evaporated and the residue purified by column chromatography (silica gel, hexane/ethyl acetate 3:1) to yield the title compound (110 mg, 85.3% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography (silica gel, hexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-11ca5e69572648439f9b95e2087dbef5
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Linked notes

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