Acetyl chloride → 1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 1920265Notes

Reaction equation

HRID 1920265 reaction equation
C(Cl)(=O)C.[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:15]([CH2:21][CH2:22][CH3:23])=[N:14][C:13]=1[C:24]#[N:25]>C(O)C>[CH3:19][CH:18]([CH3:20])[CH2:17][N:16]1[C:12]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[C:24]([NH2:25])[C:13]=2[N:14]=[C:15]1[CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 585001375-(2-aminophenyl)-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile

Product 1

HCID 111502461-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amineYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, a solution of acetyl chloride (15 mmol) in anhydrous ethanol (50 mL) was stirred for 15 minutes and then added to 5-(2-aminophenyl)-1-(2-methylpropyl)-2-propyl-1H-imidazole-4-carbonitrile (2.75 g). The reaction was heated at reflux under nitrogen for 16 hours, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was partitioned between 2M aqueous sodium carbonate and chloroform. The aqueous layer was separated and extracted twice with chloroform. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product (2.81 g) was purified by automated flash chromatography (eluting with 0% to 20% CMA in chloroform) and then recrystallized from acetonitrile (50 mL). The crystals were dried overnight at 33 Pa and 98° C. to provide 1.65 g of 1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as white needles, mp 191-192° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux under nitrogen for 16 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between 2M aqueous sodium carbonate and chloroform
  5. customThe aqueous layer was separated
  6. extractionextracted twice with chloroform
  7. dry with materialThe combined organic fractions were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product (2.81 g) was purified by automated flash chromatography (eluting with 0% to 20% CMA in chloroform)
  11. customrecrystallized from acetonitrile (50 mL)
  12. customThe crystals were dried overnight at 33 Pa and 98° C.

Sources & evidence

ORD record
ord-3bdfedca892547968edbc2c293dcbfb0
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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