反应详情

N-Hydroxybenzenecarboximidoyl chloride (13.7 g) was prepared according to the method described in Part D of Example 1 by reacting benzaldehyde oxime (11.5 g, 94.9 mmol) in DMF (20 mL) with N-chlorosuccinimide (12.6 g, 94.9 mmol) and was obtained as a white solid. Triethylamine (0.69 mL, 4.97 mmol) was added to a solution of N-hydroxybenzenecarboximidoyl chloride (644 mg, 4.14 mmol) and 1-allyl-4-chloro-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline (prepared as described in Part C of Example 1, 1.00 g, 3.32 mmol) in dichloromethane (50 mL) at room temperature. The solution was stirred overnight and then was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel to afford 4-chloro-2-(ethoxymethyl)-1-[(3-phenyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline as a pale yellow solid (1.19 g).

1. customwas obtained as a white solid
2. washwas washed with saturated aqueous sodium bicarbonate
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude product was purified by flash chromatography on silica gel