Quinazoline compound as well as preparation method and application thereof
A compound, technology of dimethoxyquinazoline, applied in the field of medicine
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Embodiment 1
[0072] Preparation of 6,7-dimethoxy-4-(1,2,3,4-tetrahydroquinoline-6oxy)quinazoline (Ⅱ)
[0073] Add 22.5g (100.2mmol) of 4-chloro-6,7-dimethoxyquinazoline, 250ml of butanone, 16.5g (51mmol) of tetrabutylammonium bromide, and 20% sodium hydroxide solution into a 500ml round bottom bottle 120ml, stirred at room temperature for 2 minutes, another 15g (100.5mmol) of 6-hydroxy-1,2,3,4-tetrahydroquinoline was taken, stirred, heated to reflux, reacted for 1 hour, TLC followed the reaction (petroleum ether was used as the developer : ethyl acetate=2.5:2.5), complete reaction. post-processing.
[0074] The reaction solution was transferred to a separatory funnel, the water layer was separated, the organic layer was washed twice by adding 50 ml of water, the organic layer was left to stand, and light yellow crystals slowly precipitated, filtered to obtain 28 g of dry solid. Butanone was refined to obtain 22g of pure product. Yield: 65.3%.
[0075] 1 HNMR (600MHz, CDCl 3 )δ8.65(s,...
Embodiment 2
[0076] Embodiment 2 (synthesis of ZLZ-KZL-01)
[0077] Add 0.5g (1.5mmol) of 6,7-dimethoxy-4-(1,2,3,4-tetrahydroquinoline-6oxy)quinazoline and 10ml of chloroform into a 100ml round bottom bottle, dissolve, Stir at room temperature, take another 0.45g (3.0mmol) of 2-isopropylphenylisocyanate in 2ml of chloroform until dissolved, slowly add to the round bottom bottle after dissolving, react at room temperature for 1 hour, follow the reaction by TLC (the developer is petroleum Ether: ethyl acetate = 1.5:3.0), after 2 hours of reaction at room temperature, it became light yellow and turbid, and it was reacted at room temperature for 48 hours before post-treatment.
[0078] The reaction solution was transferred to a separatory funnel, 10ml of water was added to the chloroform layer and shaken and washed twice, the chloroform layer was washed once with 5ml of saturated sodium bicarbonate solution, and 10ml of water was added to shake and washed twice, and the chloroform layer was wa...
Embodiment 3
[0080] Embodiment 3 (synthesis of ZLZ-KZL-02)
[0081] Add 0.5g (1.5mmol) of 6,7-dimethoxy-4-(1,2,3,4-tetrahydroquinoline-6oxy)quinazoline and 10ml of chloroform into a 100ml round bottom bottle, dissolve, Stir at room temperature, take another 0.47g (3.0mmol) of tert-octyl isocyanate in 2ml of chloroform until dissolved, slowly add to the round bottom bottle after dissolving, react at room temperature for 1 hour, follow the reaction by TLC (developing agent is petroleum ether: acetic acid Ethyl ester=2.5:2.5), react at room temperature for 30 hours, and post-treatment.
[0082] The reaction solution was transferred to a separatory funnel, 10ml of water was added to the chloroform layer and shaken and washed twice, the chloroform layer was washed once with 5ml of saturated sodium bicarbonate solution, and 10ml of water was added to shake and washed twice, and the chloroform layer was washed with anhydrous magnesium sulfate 1.5 g was dried for 1 hour, filtered, most of the chlor...
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