Water → HCID 69332660, compound

HRID 915073Notes

Reaction equation

HRID 915073 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:5]([C:12]2[CH:13]=[CH:14][C:15](=[O:21])[N:16]([CH:18]([CH3:20])[CH3:19])[N:17]=2)=[N:6][C:7]=1S(C)(=O)=O.[CH3:28][O-:29].[Na+].O>CO.CC(C)=O>[NH2:1][C:2]1[N:3]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:5]([C:12]2[CH:13]=[CH:14][C:15](=[O:21])[N:16]([CH:18]([CH3:20])[CH3:19])[N:17]=2)=[N:6][C:7]=1[O:29][CH3:28]

Participants

6

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 69331470HCID 69331470, compound

Product 1

HCID 69332660HCID 69332660, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

A suspension of 6-[5-amino-6-(methylsulfonyl)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (205 mg) and sodium methoxide (57.7 mg) in MeOH (0.6 m) was refluxed for 24 hours. Water (3 ml) was added to the reaction mixture to give a precipitate. The precipitate was collected by filtration and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (60:40 v/v) to give a solid. The solid was suspended in acetone and collected by filtration to give 6-(5-amino-6-methoxy-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (154 mg).

Workup

  1. temperaturewas refluxed for 24 hours
  2. customto give a precipitate
  3. filtrationThe precipitate was collected by filtration
  4. custompurified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (60:40 v/v)
  5. customto give a solid
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-04e7e5e90e804de9aa721789a39d1208
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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