Citric Acid → HCID 49764315, compound

HRID 1677406Notes

Reaction equation

HRID 1677406 reaction equation
C([O:3][C:4](OCC)([CH3:28])[C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)[N:14]=2)[NH:9][CH:8]=1)=[O:6])C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:27][O:26][C:18]1[CH:17]=[C:16]([C:13]2[N:14]=[C:15]3[C:7]([C:5](=[O:6])[C:4](=[O:3])[CH3:28])=[CH:8][NH:9][C:10]3=[N:11][CH:12]=2)[CH:21]=[C:20]([O:22][CH3:23])[C:19]=1[O:24][CH3:25]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 442067082,2-Diethoxy-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one

Product 1

HCID 49764315HCID 49764315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2-Diethoxy-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one (0.027 mg, 0.06 mM) was dissolved in 3 ml dichloromethane and 0.3 gm silica gel was added followed by 0.03 ml 10% aqueous citric acid solution. After stirring overnight 0.03 ml trifluoroacetic acid was added and stirred again overnight. To the orange mixture was added aqueous sodium bicarbonate, the mixture filtered and the silica gel rinsed with a methanol/dichloromethane mixture (20/80). The rinses were concentrate and the oil purified on a preparative thin layer chromatography plate eluting with methanol/dichloromethane (4/96). The product was dissolved in acetonitrile to induce crystallization, stripped and dried overnight at 2 torr in a vacuum oven at 60° C. to give 1-[2-(3,4,5-Trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propane-1,2-dione. (M+H)+=356.

Workup

  1. addition0.3 gm silica gel was added
  2. additionwas added
  3. filtrationthe mixture filtered
  4. washthe silica gel rinsed with a methanol/dichloromethane mixture (20/80)
  5. concentrationThe rinses were concentrate
  6. customthe oil purified on a preparative thin layer chromatography plate
  7. washeluting with methanol/dichloromethane (4/96)
  8. dissolutionThe product was dissolved in acetonitrile
  9. customcrystallization
  10. customdried overnight at 2 torr in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-4c47dcfbe4d041f0a77409e506b2d8ce
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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