Imiquimod → 8-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9448

Reaction equation

HRID 9448 reaction equation
[CH3:1][CH:2]([CH3:18])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:19][C:13]1[CH:12]=[CH:11][C:10]2[N:9]=[C:8]([NH2:17])[C:7]3[N:6]=[CH:5][N:4]([CH2:3][CH:2]([CH3:18])[CH3:1])[C:16]=3[C:15]=2[CH:14]=1

Participants

4

Reactant 2

HCID 57469ImiquimodHCID 67184N-bromobutanimide

Product 1

HCID 111745978-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amineYield 22.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (30.0 g, 125 mmol) in chloroform (620 mL) was heated to 50° C., and N-bromosuccinimide (28.8 g, 162 mmol) was added in five portions over a period of five minutes. The resulting dark red solution was heated at reflux for 45 minutes, allowed to cool to ambient temperature, and stirred for one hour. A precipitate formed, was isolated by filtration, and was washed with water and diethyl ether to provide 9.0 g of 8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]-quinolin-4-amine as a solid.

Workup

  1. temperatureThe resulting dark red solution was heated
  2. temperatureat reflux for 45 minutes
  3. customA precipitate formed
  4. customwas isolated by filtration
  5. washwas washed with water and diethyl ether

Sources & evidence

ORD record
ord-a0aab8bc0b124b31a57accf5057cc740
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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