3-Amino-5-methylisoxazole → 5-Acetyl-2-ethyl-4-[(5-methylisoxazol-3-yl)amino]-6-phenylpyridazin-3(2H)-one

HRID 1725542

Reaction equation

HRID 1725542 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:27]=[C:26]([CH3:28])[O:25][N:24]=1>C(O)C>[C:1]([C:4]1[C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[NH:19][C:23]1[CH:27]=[C:26]([CH3:28])[O:25][N:24]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 661723-Amino-5-methylisoxazoleHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 684884685-Acetyl-2-ethyl-4-[(5-methylisoxazol-3-yl)amino]-6-phenylpyridazin-3(2H)-oneYield 37.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 80 mg (0.278 mmol) of 5-acetyl-2-ethyl nitro-6-phenylpyridazin-3(2H)-one (Dal Piaz, V et al., J. Med. Chem. 1997, 40, 1417) in ethanol (4 mL), 3-amino-5-methylisoxazol (96 mg, 0.978 mmol) was added. The resulting mixture was stirred, at room temperature for four days and the final product was collected by filtration and washed with diethylether to yield the title compound (35 mg, 37.2% yield).

Workup

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

Sources & evidence

ORD record
ord-ca5665ef37d84a5b8462c7b3679d20f7
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Linked notes

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