Trifluoroacetic acid → HCID 57550526, compound

HRID 1097565Notes

Reaction equation

HRID 1097565 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH:10][C:11]1[N:12]([CH2:43][CH:44]([CH3:46])[CH3:45])[C:13]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([N:23](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)[C:14]=2[N:42]=1)[CH3:9].[OH-].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:8]([NH:10][C:11]1[N:12]([CH2:43][CH:44]([CH3:45])[CH3:46])[C:13]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([NH2:23])[C:14]=2[N:42]=1)[CH3:9]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 68955650HCID 68955650, compound

Product 1

HCID 57550526HCID 57550526, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Trifluoroacetic acid (20 mL) was added to N2-ethyl-N4,N4-bis(4-methoxybenzyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine (2.0 g, 3.8 mmol), and the reaction was heated at 50° C. for four hours and allowed to cool to ambient temperature. Aqueous sodium hydroxide (6 M) was added to adjust the solution to pH 9, and then dichloromethane and saturated aqueous sodium bicarbonate were added. The organic layer was separated and washed twice with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered through a layer of CELITE filter agent, and concentrated under reduced pressure. The residue was purified twice by automated flash chromatography (silica cartridge, eluting with 12% methanol in dichloromethane followed by silica cartridge, eluting with 3-12% methanol in dichloromethane). The resulting product was recrystallized from acetonitrile containing a few drops of methanol, combined with material from another run, and recrystallized again using the same solvents to provide 210 mg of N2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine as beige needles, mp 188-190° C.

Workup

  1. temperatureto cool to ambient temperature
  2. customThe organic layer was separated
  3. washwashed twice with aqueous sodium bicarbonate
  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 twice by automated flash chromatography (silica cartridge, eluting with 12% methanol in dichloromethane followed by silica cartridge, eluting with 3-12% methanol in dichloromethane)
  8. customThe resulting product was recrystallized from acetonitrile containing a few drops of methanol
  9. customrecrystallized again

Sources & evidence

ORD record
ord-3054a529ae1b421eb58e805b7ca88c0a
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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