Hydrogen Peroxide → HCID 67370993, compound

HRID 1910899Notes

Reaction equation

HRID 1910899 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([N:9]2[C:13]3([C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[CH2:14][N:15]4[CH:21]=[CH:20][CH:19]=[C:16]4[C:17](=[O:18])[N:12]3[CH2:11][CH2:10]2)=[O:8])=[CH:5][O:4][N:3]=1.[OH:28]O.O>C(Cl)Cl.C[Re](=O)(=O)=O>[CH3:1][C:2]1[C:6]([C:7]([N:9]2[C:13]3([C:22]4[CH:23]=[N+:24]([O-:28])[CH:25]=[CH:26][CH:27]=4)[CH2:14][N:15]4[CH:21]=[CH:20][CH:19]=[C:16]4[C:17](=[O:18])[N:12]3[CH2:11][CH2:10]2)=[O:8])=[CH:5][O:4][N:3]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 53373164HCID 53373164, compound

Product 1

HCID 67370993HCID 67370993, compound

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-10a-(pyridin-3-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (15 mg, 0.041 mmol) in CH2Cl2 (0.5 mL) was added methyltrioxorhenium (VII) (1 mg, 0.004 mmol) followed by hydrogen peroxide (30% aqueous solution, 70 μL, 0.62 mmol). The resulting solution was stirred vigorously at room temperature. After 4.5 hours the reaction was complete (monitored by LCMS). Water (2 mL) was then added and the mixture extracted with CH2Cl2 (3×1 mL). The extracts were combined, dried (MgSO4), filtered and concentrated in vacuo to give an oil that was purified by flash chromatography (Biotage SP4, 4 g cartridge, gradient 0 to 10% methanol in CH2Cl2). The compound 1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-10a-(1-oxidopyridin-3-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (78) was isolated as a colourless oil (2 mg, yield 12%).

Workup

  1. extractionthe mixture extracted with CH2Cl2 (3×1 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give an oil that
  6. customwas purified by flash chromatography (Biotage SP4, 4 g cartridge, gradient 0 to 10% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-296e2ce2871049cbb0bacf51591808af
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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