Aldoxime → 4-chloro-2-(ethoxymethyl)-1-[3-(3-methylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinoline

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In the presence of triethylamine (5.2 mL, 10.7 mmol) in a solution of THF (50 mL), 4-chloro-2-(ethoxymethyl)-1-pent-4-ynyl-1H-imidazo[4,5-c]quinoline (prepared as described in Part F of Example 6, 3.50 g, 10.7 mmol) was reacted with N-hydroxyethanimidoyl chloride that was generated from acetaldehyde oxime (1.90 g, 32.1 mmol) and N-chlorosuccinimide (4.30 g, 32.1 mmol) using the method described in Part B of Example 5. The crude product was purified by flash chromatography (silica gel, gradient elution with 4:1 to 2:3 hexanes/ethyl acetate). The appropriate fractions were combined and concentrated to provide a solid that was triturated with diethylether. The solid was isolated by filtration and dried to yield 4-chloro-2-(ethoxymethyl)-1-[3-(3-methylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinoline (1.87 g) as a white solid.

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