[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=[C:6]1[CH2:18][CH2:19][CH3:20])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:33].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl.O>[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:33])[C:8]=2[N:7]=[C:6]1[CH2:18][CH2:19][CH3:20])([CH3:3])[CH3:2]A solution of N-isopropyl-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (2.48 g, 9.24 mmol) in 75 mL of chloroform was cooled in a cold water bath. The solution was treated with MCPBA (3.32 g, 11.6 mmol) over 6 min. The reaction was allowed to come to ambient temperature. After 1.5 h, TLC showed complete conversion to the 5-N-oxide intermediate. The reaction mixture was again cooled in a cold water bath and then treated with concentrated ammonium hydroxide solution (30 mL, 30%) and stirred rapidly. The reaction mixture was treated with p-toluenesulfonyl chloride (1.85 g, 9.70 mmol) over 5 min. The reaction was allowed to come to ambient temperature. After 30 min, the reaction mixture was diluted with 50 mL of chloroform and 30 mL of water and the phases were separated. The organic portion was washed with 5% Na2CO3 solution (30 mL), water (30 mL) and brine (30 mL). The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to yield a light brown foam. The material was purified by chromatography (SiO2, 97:3 CHCl3:MeOH) and recrystallized from EtOAc to yield 1.39 g of N1-isopropyl-2-propyl-1H-imidazo[4,5-c]quinoline-1,4-diamine as amber crystals.
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