Quinoline compounds and their preparation methods and applications
A compound, technology of dihydroquinoline, applied in the field of medicine
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Embodiment 1
[0078] Preparation of 6,7-dimethoxy-4-(1,2,3,4-tetrahydroquinoline-6oxy)quinoline (Ⅱ)
[0079] Add 22.5g (100.6mmol) of 4-chloro-6,7-dimethoxyquinoline, 15g (100.5mmol) of 6-hydroxy-1,2,3,4-tetrahydroquinoline into a 250ml round bottom bottle, N -Methylpyrrolidone (NMP) 100ml, stir evenly to dissolve, add 33.9g (301.8mmol) of potassium tert-butylate three times under ice bath, heat to 100°C, stir for about 16 hours, follow the reaction by TLC (the developer is petroleum Ether: ethyl acetate = 2.5:2.5), after the reaction is completed, carry out post-processing. NMP was evaporated under reduced pressure, and the residue was washed with water to obtain a pale yellow solid, which was recrystallized from methanol-petroleum ether, filtered, and dried to obtain 19 g of pure product. Yield: 56.2%.
[0080] 1 HNMR(600MHz,DMSO)δ8.43(d,J=5.2Hz,1H),7.49(s,1H),7.36(s,1H),6.77(d,J=2.7Hz,1H),6.76(s, 1H),6.53(d,J=8.2Hz,1H),6.40(d,J=5.2Hz,1H),5.74(s,1H),3.94(s,3H),3.93(s,3H),3.22- 3.19(m...
Embodiment 2
[0081] Embodiment 2 (synthesis of KL-01)
[0082] Add 0.5g (1.5mmol) of 6,7-dimethoxy-4-(1,2,3,4-tetrahydroquinoline-6oxy)quinoline and 10ml of chloroform into a 100ml round bottom bottle, dissolve and keep at room temperature Stir, and take another 0.47g (3.0mmol) of tert-octyl isocyanate in 2ml of chloroform until dissolved, slowly add it to the round bottom bottle after dissolving, react at room temperature for 1 hour, follow the reaction by TLC (developing agent is dichloromethane: methanol =4.5:0.5), reacted at room temperature for 70 hours, and post-treated.
[0083] 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, and evaporated to dry...
Embodiment 3
[0085] Embodiment 3 (synthesis of KL-02)
[0086]Add 0.5g (1.5mmol) of 6,7-dimethoxy-4-(1,2,3,4-tetrahydroquinoline-6oxy)quinoline and 10ml of chloroform into a 100ml round bottom bottle, dissolve and keep at room temperature Stir, and take another 0.44g (3.0mmol) of 2-ethylphenyl isocyanate in 2ml of chloroform until dissolved, slowly add it to the round bottom bottle after dissolving, react at room temperature for 1 hour, follow the reaction by TLC (the developer is ethyl acetate Ester:methanol=4.7:0.3), react at room temperature for 65 hours, and post-treatment.
[0087] 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, and evaporated to dr...
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