HCID 18783936, compound → 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 1108640Notes

Reaction equation

HRID 1108640 reaction equation
C([NH:8][C:9]1[C:18]2[N:19]=[CH:20][N:21]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26]C(OC(C)(C)C)=O)[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1)C1C=CC=CC=1>C(O)=O.[OH-].[Pd+2].[OH-].[C]>[NH2:26][CH2:25][CH2:24][CH2:23][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

4

Reactant 1

HCID 18783936HCID 18783936, compound

Product 1

HCID 154537751-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amineYield 36.5%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 284Formic AcidSolvent

Procedure

67 mg (0.150 mmol) of 4-Benzylamino-1-[4-(tert-butoxycarbonylamino)butyl]-1H-imidazo[4,5-c]quinoline was dissolved in 5 ml of formic acid. 0.15 g of 20% palladium hydroxide-carbon was added thereto and the mixture was refluxed for 2 days under heating. The reaction mixture was filtered and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol:32% acetic acid=6:3:1 (v/v)) to obtain the acetic acid salt of the object. The product was treated with alkali and the solid was collected by filtration to obtain 14 mg (0.0548 mmol) of 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinoline-4-amine shown below as faint brown powder. ##STR47## The physicochemical properties of this compound was in agreement with those of the compound of Example 17.

Workup

  1. temperaturethe mixture was refluxed for 2 days
  2. temperatureunder heating
  3. filtrationThe reaction mixture was filtered
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol:32% acetic acid=6:3:1 (v/v))
  6. customto obtain the acetic acid salt of the object
  7. additionThe product was treated with alkali and the solid
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-05430e8117c04d4db2f5c89550fea998
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

Loading…