5-Amino-3-methylisoxazole → HCID 68487011, compound

HRID 1725538Notes

Reaction equation

HRID 1725538 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[O:27][N:26]=[C:25]([CH3:28])[CH: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[O:27][N:26]=[C:25]([CH3:28])[CH:24]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 845905-Amino-3-methylisoxazoleHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 68487011HCID 68487011, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 200 mg (0.696 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 (10 mL), 5-amino-3-methylisoxazole (204 mg, 2.088 mmol) was added. The resulting mixture was stirred at 50° C. for four days. The solvent was evaporated and the residue purified by column chromatography (silica gel, hexane/ethyl acetate 2:1) to yield the title compound (35 mg, 14.9% yield).

Workup

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

Sources & evidence

ORD record
ord-d87859730cf544fea481c4226b110db2
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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