N,N-Bis(phenylmethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine → Imiquimod

HRID 1608663Notes

Reaction equation

HRID 1608663 reaction equation
C1(C[N:8](CC2C=CC=CC=2)[C:9]2[C:18]3[N:19]=[CH:20][N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:17]=3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)=O.C(Cl)Cl.O.CO>[CH3:24][CH:23]([CH3:25])[CH2:22][N:21]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:8])[C:18]=2[N:19]=[CH:20]1

Participants

7

Reactant 1

HCID 15233091N,N-Bis(phenylmethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 57469ImiquimodYield 43.8%

Reagents, catalysts & solvents 5

HCID 9942167Palladium hydroxideCatalyst2×HCID 284Formic AcidSolventHCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Palladium hydroxide on carbon, Pearlman's catalyst, (0.25 g) was added to a solution containing N,N-bis(phenylmethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.4 g, 0.95 mmole, Example 4) in formic acid (20 mL). The reaction was heated at reflux for about 16 hours at which time more catalyst (0.2 g) was added and heating was continued until the reaction was complete as indicated by thin layer chromatography (silica gel; 5% methanol in methylene chloride). The reaction mixture was diluted with water (20 mL), methylene chloride (40 mL) and methanol (10 mL) then filtered. The filtrate layers were separated and the organic layer was concentrated under vacuum. The residue was recrystallized from dimethyl formamide then suspended in methanol and stirred before being isolated by filtration and dried to provide 0.1 g of a solid. The melting point and spectral properties of this material matched those of an authentic sample.

Workup

  1. temperatureThe reaction was heated
  2. additionwas added
  3. temperatureheating
  4. filtrationthen filtered
  5. customThe filtrate layers were separated
  6. concentrationthe organic layer was concentrated under vacuum
  7. customThe residue was recrystallized from dimethyl formamide
  8. custombefore being isolated by filtration
  9. customdried

Sources & evidence

ORD record
ord-c40b65fc12e34c68a6693eb1559aacc2
Source dataset
uspto-grants-1995_03
Patent number
US05395937

Reaction notes

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