HCID 86662052, compound → HCID 86662051, compound

HRID 869247Notes

Reaction equation

HRID 869247 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:27]=[CH:26][N:25]([CH3:28])[CH:24]=[CH:23]3)=[CH:18][CH:17]=2)[C:5]([C:12]([NH2:14])=[O:13])=[N:6][C:7]=1[C:8](O)([CH3:10])[CH3:9]>C(O)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([N:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)=[CH:20][CH:21]=2)[C:5]([C:12]([NH2:14])=[O:13])=[N:6][C:7]=1[C:8]([CH3:10])=[CH2:9]

Participants

3

Reactant 1

HCID 86662052HCID 86662052, compound

Product 1

HCID 86662051HCID 86662051, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-chloro-6-(1-hydroxy-1-methylethyl)-3-{[4-(4-methylpyrazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (Preparation Example 416) (430 mg) and acetic acid (10 mL) was stirred at 120° C. for 5 hours. After the reaction liquid was cooled, the solvent was distilled off, and water and saturated aqueous sodium hydrogen carbonate were added to neutralize. After extraction with ethyl acetate, the extract was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was washed with diisopropyl ether to give 5-chloro-6-isopropenyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (265 mg) as an orange solid.

Workup

  1. customAfter the reaction liquid
  2. temperaturewas cooled
  3. distillationthe solvent was distilled off
  4. additionwater and saturated aqueous sodium hydrogen carbonate were added
  5. extractionAfter extraction with ethyl acetate
  6. washthe extract was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. washthe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-bcf9ddc996e44d55a8b052d894570a25
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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