Formamide → Imiquimod

HRID 425255Notes

Reaction equation

HRID 425255 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].CC(N(C)C)=O.[CH:13]([NH2:15])=O.BrC1[C:26]2[N:27]=[CH:28][NH:29][C:25]=2[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]=1>O>[CH2:1]([N:29]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:13]([NH2:15])[C:26]=2[N:27]=[CH:28]1)[CH:2]([CH3:5])[CH3:3]

Participants

6

Reactant 4

HCID 713FormamideHCID 31374DimethylacetamideHCID 23665647Potassium tert-butoxideHCID 178419474HCID 178419474, compound

Product 1

HCID 57469ImiquimodYield 94.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

Potassium tert-butoxide (3.69 g, 0.033 mole), 5 mL of dimethylacetamide and 1.31 mL (0.033 mole) of formamide were added in a 50 mL round-bottomed flask, under inert atmosphere followed by stirring for 30 minutes. After addition of 4-bromo-1H-imidazo[4,5-c]quinoline (1 g, 3.3 mmoles), the mixture was heated at 140° C., followed by stirring for 2 hours and then cooled to room temperature. Then 10 mL of water were added and the reaction mixture was filtered followed by washing with abundant water and dried to give 0.75 g of 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine. Yield 75.4%.

Workup

  1. stirringby stirring for 2 hours
  2. temperaturecooled to room temperature
  3. filtrationthe reaction mixture was filtered
  4. washby washing with abundant water
  5. customdried

Sources & evidence

ORD record
ord-102afeb8a81341699bb94af6b1e93242
Source dataset
uspto-grants-2012_01
Patent number
US08106202B2

Reaction notes

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