3-(4-Methoxybenzylamino)-6-methyl-1-carboxymethyl pyrazinone → (3-Amino-6-methyl-2-oxopyrazin-1(2H)-YL)acetic acid

HRID 322547Notes

Reaction equation

HRID 322547 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:10](=[O:20])[N:11]([CH2:16][C:17]([OH:19])=[O:18])[C:12]([CH3:15])=[CH:13][N:14]=2)=CC=1>FC(F)(F)C(O)=O>[NH2:8][C:9]1[C:10](=[O:20])[N:11]([CH2:16][C:17]([OH:19])=[O:18])[C:12]([CH3:15])=[CH:13][N:14]=1

Participants

3

Reactant 1

HCID 220087443-(4-Methoxybenzylamino)-6-methyl-1-carboxymethyl pyrazinone

Product 1

HCID 22008747(3-Amino-6-methyl-2-oxopyrazin-1(2H)-YL)acetic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The pyrazinone 18-6 (900 mg) was heated at reflux in trifluoroacetic acid (20 mL) for 7 h. The volatiles were removed in vacuo and the residue was azeotroped with CH2Cl2, then EtOAc then MeOH. MeOH was added to the residue and the solution filtered to remove impurities. Removal of the methanol then afforded the title compound 18-7 which was used as such:

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was azeotroped with CH2Cl2
  3. additionMeOH was added to the residue
  4. filtrationthe solution filtered
  5. customto remove impurities
  6. customRemoval of the methanol

Sources & evidence

ORD record
ord-8b4d4be21f104dcea21508ba435f4df0
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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