HCID 22249516, compound → HCID 22249600, compound

HRID 890227Notes

Reaction equation

HRID 890227 reaction equation
[CH2:1]([CH:3]([N:6]1[C:18]2[C:17]3[N:16]=[CH:15][CH:14]=[C:13]([C:19]4[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=4[CH3:27])[C:12]=3[N:11]=[C:10]([CH3:28])[C:9]=2[CH2:8][CH2:7]1)[CH2:4][CH3:5])[CH3:2]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH2:1]([CH:3]([N:6]1[C:18]2[C:17]3[N:16]=[CH:15][CH:14]=[C:13]([C:19]4[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=4[CH3:27])[C:12]=3[N:11]=[C:10]([CH3:28])[C:9]=2[CH:8]=[CH:7]1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 1

HCID 22249516HCID 22249516, compound

Product 1

HCID 22249600HCID 22249600, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

Activated manganese dioxide (47 mg, 0.54 mmol) was added to a solution of 1-(1-ethylpropyl)-6-mesityl-4-methyl-2,3-dihydro-1H-pyrrolo[3,2-c][1,5]naphthyridine (40 mg, 0.11 mmol) in toluene (4.0 mL) and the mixture was heated under reflux for one day. After filtering through Celite, the mixture was evaporated. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane), to give the title compound (32 mg) as white crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one day
  3. filtrationAfter filtering through Celite
  4. customthe mixture was evaporated
  5. customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ed7fed6369fa4bcdb4c49dac9e63ca4a
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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