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