HCID 22249516, compound → HCID 22249600, compound

HRID 584838Notes

Reaction equation

HRID 584838 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-64e0125ed3e9442ca9a7b914a3952565
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Reaction notes

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