Water → HCID 69103551, compound

HRID 2217241Notes

Reaction equation

HRID 2217241 reaction equation
[NH2:1][C:2]1[C:3]([C:19]([NH2:21])=[O:20])=[N:4][C:5]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH:16]([CH3:18])[CH3:17])[CH:10]=2)=[C:6](Cl)[N:7]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.O.CCOC(C)=O>C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[C:3]([C:19]([NH2:21])=[O:20])=[N:4][C:5]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH:16]([CH3:18])[CH3:17])[CH:10]=2)=[C:6]([C:27]2[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)[N:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 201262(4-Methoxyphenyl)boronic acidHCID 86598204HCID 86598204, compound

Product 1

HCID 69103551HCID 69103551, compoundYield 83.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-amino-5-chloro-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-2-pyrazinecarboxamide (500 mg), (4-methoxyphenyl)boronic acid (740 mg), and Pd(PPh3)4 (56.3 mg) in 2M aq. Na2CO3 (3.25 ml) and dioxane (20 ml) was refluxed for 3 hours. Water (40 ml) and of EtOAc (30 ml) were poured into the reaction mixture and the aqueous solution was extracted with EtOAc. The organic layer was washed with water and brine, and dried over MgSO4. After filtration, the solvent was removed under reduced pressure. The residual solid was placed on a column of silica-gel and eluted with CHCl3:MeOH (25:1). The eluent was evaporated and the residue was suspended with IPE and filtrated to give 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-5-(4-methoxyphenyl)-2-pyrazinecarboxamide (512 mg) as a yellow powder.

Workup

  1. temperaturewas refluxed for 3 hours
  2. extractionthe aqueous solution was extracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure
  7. washeluted with CHCl3:MeOH (25:1)
  8. customThe eluent was evaporated
  9. filtrationfiltrated

Sources & evidence

ORD record
ord-add6d6c627c547c2be5c47b3d71da311
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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