Water → 6-[5-amino-6-(4-methyl-thiazol-2-yl)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone

HRID 915032Notes

Reaction equation

HRID 915032 reaction equation
[NH2:1][C:2]1[C:3]([C:24](=[S:26])[NH2:25])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.Cl[CH2:28][C:29]([CH3:31])=O.C([O-])(O)=O.[Na+].O>CN(C=O)C.CCOC(C)=O.CCCCCC>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)=[N:4][C:3]=1[C:24]1[S:26][CH:28]=[C:29]([CH3:31])[N:25]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 516892Sodium BicarbonateHCID 866009113-Amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbothioamide

Product 1

HCID 693319926-[5-amino-6-(4-methyl-thiazol-2-yl)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinoneYield 52.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbothioamide (100 mg) and 1-chloroacetone (37.9 mg) in DMF (0.27 ml) was heated at 100-105° C. for 10 hours. After cooling, sat. aq. NaHCO3 solution (0.5 ml) and water (1 ml) were added to the mixture to yield a precipitate. The precipitate was collected by filtration, dissolved in CHCl3, dried over MgSO4 and concentrated under reduced pressure to give a residue. The residue was subjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (60:40 v/v) to give 6-[5-amino-6-(4-methyl-thiazol-2-yl)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone as a solid (58 mg).

Workup

  1. temperatureAfter cooling
  2. customto yield a precipitate
  3. filtrationThe precipitate was collected by filtration
  4. dissolutiondissolved in CHCl3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue

Sources & evidence

ORD record
ord-ed4c12ac284e4e0b808813172df1dd9b
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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