HCID 22024596, compound → HCID 22024494, compound

HRID 500989Notes

Reaction equation

HRID 500989 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:13]([OH:17])[CH2:14][CH2:15][CH3:16])=[C:9]([CH2:11][CH3:12])[N:10]=2)[CH:5]=[CH:6][N:7]=1>C(OCC)(=O)C.C(Cl)Cl.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:13](=[O:17])[CH2:14][CH2:15][CH3:16])=[C:9]([CH2:11][CH3:12])[N:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 1

HCID 22024596HCID 22024596, compound

Product 1

HCID 22024494HCID 22024494, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

The resulting 1-(8-chloro-2-ethylimidazo[1,2-a]pyrazin-3-yl)-1-butanol was dissolved in ethyl acetate (4 mL) and methylene chloride (1 mL), then activated manganese (IV) oxide (3 g) was added thereto, and the mixture was heated under stirring at 60° C. for 5 hours. After being allowed to cool, the reaction mixture was filtered and washed with ethyl acetate, and then the filtrates were combined and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3) to give the title compound (226 mg) as white crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto cool
  3. filtrationthe reaction mixture was filtered
  4. washwashed with ethyl acetate
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-8a75eb283eea4e508ba53ae6f570740d
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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