Water → HCID 86600905, compound

HRID 915009Notes

Reaction equation

HRID 915009 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[NH:12][C:13](=[O:22])[O:14][C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5]1)([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:26][C:27]([O:29][CH3:30])=[O:28].O>CN(C=O)C.C(Cl)(Cl)Cl>[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[N:12]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[C:13](=[O:22])[O:14][C:15]=2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:5]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 69332645HCID 69332645, compound

Product 1

HCID 86600905HCID 86600905, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Under nitrogen atmosphere, 2-isopropyl-6-(2-oxo-5-phenyl-2,3-dihydro-oxazol-4-yl)-3(2H)-pyridazinone (100 mg) was added to a suspension of NaH (60% dispersion in mineral oil) (14 mg) in DMF (0.3 ml) at 20-25° C. and the mixture was stirred at the same temperature for 30 minutes. Methyl bromoacetate (0.0035 ml) was added to the mixture and stirred at 70-75° C. for 7 hours. After an addition of water (5 ml), an aqueous solution was removed by decantation to give a residue. The residue was dissolved in CHCl3, dried over MgSO4, concentrated under reduced pressure and subjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (40:60 v/v) to give methyl [4-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-5-phenyl-oxazol-3(2H)-yl]-acetate as a solid (64 mg).

Workup

  1. stirringstirred at 70-75° C. for 7 hours
  2. customan aqueous solution was removed by decantation
  3. customto give a residue
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. additionsubjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (40:60 v/v)

Sources & evidence

ORD record
ord-a49a5cd81b044dcfbf3db9c5cd1e7cd0
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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