4-benzylamino-1-[3-(tert-butoxycarbonylamino)propyl]-1H-imidazo[4,5-c]quinoline → 1-(3-aminopropyl)-1H-imidazo[4,5-c]quinoline-4-amine

HRID 1108634Notes

Reaction equation

HRID 1108634 reaction equation
C([NH:8][C:9]1[C:18]2[N:19]=[CH:20][N:21]([CH2:22][CH2:23][CH2:24][NH:25]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]>[NH2:25][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 187839524-benzylamino-1-[3-(tert-butoxycarbonylamino)propyl]-1H-imidazo[4,5-c]quinoline

Product 1

HCID 187839731-(3-aminopropyl)-1H-imidazo[4,5-c]quinoline-4-amineYield 41.7%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 284Formic AcidSolvent

Procedure

30 mg (0.0695 mmol) of 4-benzylamino-1-[3-(tert-butoxycarbonylamino)propyl]-1H-imidazo[4,5-c]quinoline was dissolved in 3 ml of formic acid. 0.1 g of 20% palladium hydroxide-carbon was added thereto and the mixture was refluxed under heating for one day. The reaction mixture was filtered and the filtrate was evaporated to distill off the solvent under reduced pressure. The resulting 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 thus obtained product was subjected to treatment with alkali to obtain the free base. The precipitate thus formed was collected by filtration to obtain 7 mg (0.0290 mmol) of 1-(3-aminopropyl)-1H-imidazo[4,5-c]quinoline-4-amine shown below as faint brown powder. ##STR40## The physicochemical data of this compound was in agreement with compound of Example 5.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for one day
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was evaporated
  5. distillationto distill off the solvent under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform: methanol:32% acetic acid=6:3:1 (v/v))
  7. customto obtain the acetic acid salt of the object
  8. customto obtain the free base
  9. customThe precipitate thus formed
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-385ecafbf5eb495f8f66c7306af9c2dd
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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