Acetic Acid → HCID 86662048, compound

HRID 869241Notes

Reaction equation

HRID 869241 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9].C(O)(=O)C.OO.[OH-:28].[Na+].[OH2:30]>O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+].C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:21])(=[O:30])=[O:28])=[CH:16][CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 86662049HCID 86662049, compound

Product 1

HCID 86662048HCID 86662048, compound

Reagents, catalysts & solvents 2

HCID 150191Sodium Tungstate DihydrateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-chloro-6-ethyl-3-{[4-(methylsulfanyl)phenyl]amino}pyrazine-2-carboxamide (Preparation Example 394) (92 mg) and acetic acid (2.5 mL), sodium tungstate dihydrate (29 mg) and 30% hydrogen peroxide solution (0.15 mL) were added and stirred at room temperature for 30 minutes. After water and ethyl acetate were added to the reaction liquid, 1M aqueous sodium hydroxide was added and stirred for 30 minutes, and the reaction liquid was partitioned. After drying over anhydrous sodium sulfate, the organic layer was filtered and concentrated. The resulting residue was washed with ethyl acetate to give 5-chloro-6-ethyl-3-{[4-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide (103 mg).

Workup

  1. additionwere added
  2. additionwas added
  3. stirringstirred for 30 minutes
  4. customthe reaction liquid
  5. customwas partitioned
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. filtrationthe organic layer was filtered
  8. concentrationconcentrated
  9. washThe resulting residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-0fb30af71a7b451293bb1f7177a08a56
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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