Acetic Acid → Ethyl 3-(7-ethyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxalin-1-yl)propanoate

HRID 72746Notes

Reaction equation

HRID 72746 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]1[C:14]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:15][CH:16]=[C:9]1[C:8](=[O:24])[NH:7]2)(=O)[CH3:2].C(O)(=O)C>[OH-].[OH-].[Pd+2].[H][H]>[CH2:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]1[C:14]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:15][CH:16]=[C:9]1[C:8](=[O:24])[NH:7]2)[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59198600Ethyl 3-(7-acetyl-4-oxo-4,5-dihydroimidazo[1,5-a]-quinoxalin-1-yl)propanoate

Product 1

HCID 59198574Ethyl 3-(7-ethyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxalin-1-yl)propanoate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of ethyl 3-(7-acetyl-4-oxo-4,5-dihydroimidazo[1,5-a]-quinoxalin-1-yl)propanoate as synthesized in above Example 183, 131 mg, Pearlman's catalyst 100 mg and acetic acid 5 mL was stirred in hydrogen atmosphere at room temperature for 43 hours. Then 75 mg of Pearlman's catalyst was added and the reaction liquid was mildly heated. Twenty-two hours later, the reaction liquid was filtered through Celite, and 30 mL of water was added to the filtrate. The precipitate was recovered by filtration, washed with water and dried in flowing air under heating to provide 65 mg of the title compound.

Workup

  1. customthe reaction liquid
  2. temperaturewas mildly heated
  3. customTwenty-two hours later, the reaction liquid
  4. filtrationwas filtered through Celite, and 30 mL of water
  5. additionwas added to the filtrate
  6. filtrationThe precipitate was recovered by filtration
  7. washwashed with water
  8. customdried
  9. temperatureunder heating

Sources & evidence

ORD record
ord-d68347b711004290a7f9e1c96d17da84
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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