1-Bromo-2-methylpropane → Imiquimod

HRID 1292480Notes

Reaction equation

HRID 1292480 reaction equation
[NH:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[C:5]([NH2:14])[C:4]=2[N:3]=[CH:2]1.[H-].[Na+].[CH2:17](Br)[CH:18]([CH3:20])[CH3:19]>CN(C)C=O.O>[CH3:17][CH:18]([CH3:20])[CH2:19][N:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[C:5]([NH2:14])[C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 178508172HCID 178508172, compound

Product 1

HCID 57469Imiquimod

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of 1.0 g (0.0054 mole) of 1H-imidazo[4,5-c]quinolin-4-amine in 10 mL of N,N-dimethylformamide was added 0.15 g (0.0059 mole) of sodium hydride. To this stirred mixture was added 0.74 g (0.0054 mole) of isobutyl bromide. After 30 minutes the mixture was heated at about 100° C. for one hour. The mixture was cooled to about 20° C., diluted with 20 mL of water, and the solid was separated by filtration. Recrystallization from N,N-dimethylformamide provided the known antiviral agent 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. temperatureThe mixture was cooled to about 20° C.
  2. customthe solid was separated by filtration
  3. customRecrystallization from N,N-dimethylformamide

Sources & evidence

ORD record
ord-b60b54826e2947dcbcb46cf1c62c8de2
Source dataset
uspto-grants-1998_05
Patent number
US05756747

Reaction notes

Loading…