5-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one → HCID 67109233, compound

HRID 1725535Notes

Reaction equation

HRID 1725535 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].[CH3:22][O:23][C:24]([C:26]1[CH:27]=[CH:28][C:29](N)=[C:30]2[C:35]=1[N:34]=[CH:33][CH:32]=[CH:31]2)=[O:25]>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:29]1[CH:28]=[CH:27][C:26]([C:24]([O:23][CH3:22])=[O:25])=[C:35]2[C:30]=1[CH:31]=[CH:32][CH:33]=[N:34]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-oneHCID 14939326HCID 14939326, compound

Product 1

HCID 67109233HCID 67109233, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
126 °C

Procedure

A mixture of (160 mg, 0.556 mmol) of 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417), 5-aminoquinoline-8-carboxilic acid methyl ester (226 mg, 1.114 mmol) (Preparation 99) and ethanol (8 mL) was introduced in the microwave oven. The mixture was stirred at 126.0° C. during 45 minutes. The solvent was evaporated and the residue purified by column chromatography (silica gel, dichloromethane/methanol 100:1) and preparative HPLC/MS to yield the title compound (7 mg, 3% yield).

Workup

  1. additionwas introduced in the microwave oven
  2. customThe solvent was evaporated
  3. customthe residue purified by column chromatography (silica gel, dichloromethane/methanol 100:1) and preparative HPLC/MS

Sources & evidence

ORD record
ord-8c849e366e0f41328ca86742b2e090ed
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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