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

Participants

Reaction Conditions

Reaction Steps

N-Hydroxybenzenecarboximidoyl chloride (prepared as described in Part A of Example 2, 2.61 g, 16.8 mmol) was added to a solution of 4-chloro-2-(ethoxymethyl)-1-pent-4-ynyl-1H-imidazo[4,5-c]quinoline (prepared as described in Part F of Example 6, 2.90 g, 8.39 mmol) and triethylamine (3.50 mL, 25.2 mmol) in dichloromethane at 6° C. The solution was heated at 50° C. under a nitrogen atmosphere for 4 hours. The solution was diluted with dichloromethane, transferred to a separatory funnel, washed with water and brine, dried over sodium sulfate, filtered, and concentrated to an oil. The oil was triturated with hexanes and the solvent was decanted. The oil was triturated with diethyl ether and a solid formed that was isolated by filtration to provide 4-chloro-2-(ethoxymethyl)-1-[3-(3-phenylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinoline (1.98 g). The filtrate was purified by flash chromatography (silica gel, gradient elution from 7:3 to 1:1 hexanes/ethyl acetate) to provide an additional 0.24 g of product. The total amount of 4-chloro-2-(ethoxymethyl)-1-[3-(3-phenylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinoline isolated was 2.22 g.

Provenance & Evidence