Carbon Dioxide → HCID 66734099, compound

HRID 1929718Notes

Reaction equation

HRID 1929718 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][C:16](I)=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Mg]Br)C.[C:36](=[O:38])=[O:37].O>C1COCC1.CC(=O)OCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][C:16]([C:36]([OH:38])=[O:37])=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 66734220HCID 66734220, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 66734099HCID 66734099, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (−30° C.) solution of 3-ethyl-1-iodo-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (500 mg; 0.910 mmol) in anhydrous THF (10 ml) was added dropwise 1M ethylmagnesium bromide in THF (2.0 ml; 2 mmol). The resulting colorless suspension was allowed to warm-up to rt in 30 min., and was again cooled to −35° C. before continuous injection of carbon dioxide during 2 h. Water and EA were then added, and the resulting reaction mixture was allowed to warm-up to rt. The organic layer was further washed with aq. sat. NH4Cl, dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure to give the expected product 3-ethyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-1,7-dicarboxylic acid 7-tert-butyl ester as a colorless foam (350 mg; 0.748 mmol; 82%).

Workup

  1. customthe resulting reaction mixture
  2. temperatureto warm-up to rt
  3. washThe organic layer was further washed with aq. sat. NH4Cl
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9b7179e7c5894a10ae717be596f317c0
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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