1H-indazol-7-amine → 5-Acetyl-2-ethyl-4-(1H-indazol-7-ylamino)-6-phenylpyridazin-3(2H)-one

HRID 1725540

Reaction equation

HRID 1725540 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].[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2N)[CH:24]=[N:23]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:29]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:30]=1[NH:22][N:23]=[CH:24]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 889011H-indazol-7-amineHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 684883025-Acetyl-2-ethyl-4-(1H-indazol-7-ylamino)-6-phenylpyridazin-3(2H)-oneYield 86.7%

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 ethanol (4 mL), 1H-indazol-7-amine (56 mg, 0.417 mmol) was added. The resulting mixture was stirred at room temperature during one hour and the final product was collected by filtration and washed with diethylether to yield the title compound (90 mg, 86.5% yield).

Workup

  1. filtrationthe final product was collected by filtration
  2. washwashed with diethylether

Sources & evidence

ORD record
ord-2f21093a501f4327b590125a11487d48
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Linked notes

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