Trifluoroacetic acid → HCID 11630397, compound

HRID 1097564Notes

Reaction equation

HRID 1097564 reaction equation
FC(F)(F)C(O)=O.COC1C=CC(C[N:15](CC2C=CC(OC)=CC=2)[C:16]2[C:25]3[N:26]=[C:27]([NH:33][CH3:34])[N:28]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:24]=3[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=2)=CC=1>[OH-].[Na+]>[CH3:34][NH:33][C:27]1[N:28]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[C:16]([NH2:15])[C:25]=2[N:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86626285HCID 86626285, compound

Product 1

HCID 11630397HCID 11630397, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

Trifluoroacetic acid (150 mL) was added to N4,N4-bis(4-methoxybenzyl)-N2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine (15 g, 29.5 mmol), and the reaction was heated at 70° C. overnight and allowed to cool to ambient temperature. Aqueous sodium hydroxide (170 mL of 12 M) was added to adjust the solution to pH 9. The resulting mixture was extracted with chloroform (3×), and the combined extracts were washed with brine (3×), dried over magnesium sulfate, filtered through a layer of CELITE filter agent, and concentrated under reduced pressure. The residue was purified by automated flash chromagraphy (silica cartridge, eluting with 0-25% methanol in ethyl acetate). The resulting product was further purified twice by flash chromatography on silica gel (eluting first with 5-10% methanol in dichloromethane and then 5-7.5% methanol in dichloromethane) to provide 3 g of N2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe resulting mixture was extracted with chloroform (3×)
  3. washthe combined extracts were washed with brine (3×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through a layer of CELITE filter agent
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by automated flash chromagraphy (silica cartridge, eluting with 0-25% methanol in ethyl acetate)
  8. customThe resulting product was further purified twice by flash chromatography on silica gel (
  9. washeluting first with 5-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-473c6a067a4949d0b4143b56db3b627a
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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