3-Methylcinnolin-5-amine → 5-Acetyl-2-ethyl-4-[(3-methylcinnolin-5-yl)amino]-6-phenylpyridazin-3(2H)-one

HRID 1725526

Reaction equation

HRID 1725526 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][C:23]1[N:24]=[N:25][C:26]2[CH:27]=[CH:28][CH:29]=[C:30](N)[C:31]=2[CH:32]=1>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:30]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:31]=1[CH:32]=[C:23]([CH3:22])[N:24]=[N:25]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 53106453-Methylcinnolin-5-amineHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 671089585-Acetyl-2-ethyl-4-[(3-methylcinnolin-5-yl)amino]-6-phenylpyridazin-3(2H)-oneYield 58.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 80 mg (0.278 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 4 ml of ethanol, 66 mg (0.417 mmol) of 3-methylcinnolin-5-amine was added. The resulting mixture was stirred at room temperature for one day. The final product was collected by filtration and purified by column chromatography (silica gel, ethyl acetate/hexane 2:1) to yield the title compound (65 mg, 58.6% yield).

Workup

  1. filtrationThe final product was collected by filtration
  2. custompurified by column chromatography (silica gel, ethyl acetate/hexane 2:1)

Sources & evidence

ORD record
ord-f88adede89cd4feabf8d6ce2adbde0bf
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Linked notes

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