Water → 6-(6-amino-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

HRID 915038Notes

Reaction equation

HRID 915038 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11](=O)[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)=[N:5]1)([CH3:3])[CH3:2].Br.Br.[NH2:23][CH2:24][C:25]([NH2:27])=[NH:26].C[O-].[Na+].O>CO.CCOC(C)=O>[NH2:27][C:25]1[N:26]=[C:11]([C:6]2[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:23][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10942334Sodium MethoxideHCID 16211382Aminoacetamidine DihydrobromideHCID 46832460HCID 46832460, compound

Product 1

HCID 693314606-(6-amino-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinoneYield 7.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-phenyl-1,2-ethanedione (300 mg), aminoacetamidine dihydrobromide (259 mg) and sodium methoxide (238 mg) in MeOH (3 ml) was stirred for 1.5 hours. Water and EtOAc were added to the reaction mixture. The organic layer was separated, and dried over MgSO4. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography eluted with a mixture of n-hexane and EtOAc. The fractions were concentrated in vacuo to obtain 6-(6-amino-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (25.6 mg) as white powder.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluted with a mixture of n-hexane and EtOAc
  6. concentrationThe fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-2f96f97846c44ad391fbe7945cf43dcb
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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