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The preparation method of 7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3h)-one

A technology of methoxyquinazoline and methoxy, which is applied in the field of organic compound synthesis, can solve the problems of too long process steps, unfavorable industrial production, cumbersome operation, etc., and achieve low-cost reaction reagents, simple operation, and high purity Effect

Inactive Publication Date: 2016-01-20
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method is cumbersome to operate, and the steps of the whole process route are too long, which is unfavorable for industrialized production

Method used

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  • The preparation method of 7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3h)-one
  • The preparation method of 7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3h)-one
  • The preparation method of 7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3h)-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The compound represented by formula II: 6-hydroxy-7-methoxyquinazolin-4-one (19.2g, 100mmol) was slowly added to 140g of 12% KOH aqueous solution, stirred and reacted for 2.0 hours until dissolved into a transparent solution , part of the water was removed under reduced pressure (until a large amount of solid precipitated, the same below), cooled, filtered, and the solid was dried to obtain the dipotassium salt of the compound represented by formula III (25.8 g, yield 96.3%).

[0041] Disperse the dipotassium salt of the compound shown in formula III (10.7g, 40mmol) in 20mLDMF, then add 5% [Bmim]BF4 ionic liquid of the dipotassium salt of the compound shown in III, add the compound shown in formula IV (X =Cl) (7.9g, 48mmol), heated to about 55-60°C for 5.0 hours, the reaction mixture was suction filtered while it was hot, and the white solid KCl formed was removed, the solvent DMF was evaporated, and 20mL of distilled water was added, stirred at room temperature and adde...

Embodiment 2

[0043] Slowly add the compound shown in formula II (11.5g, 60mmol) into 60g of 12% NaOH aqueous solution, stir and react for 2 hours, remove part of the solvent under reduced pressure, cool, filter, and dry the disodium of the compound shown in formula III Salt (13.2 g, yield 93.2%).

[0044] Disperse the disodium salt of the compound shown in formula III (7.1g, 30mmol) in 20mLTHF, then add 5% [Bmim]BF of the disodium salt of the compound shown in III 4 Ionic liquid, add compound (X=Br) (7.5g, 36mmol) shown in formula IV, heat to about 65-70°C and react for 5.0 hours, the reaction mixture is filtered while hot to remove the formed solid NaBr, and the solvent THF is evaporated Add 20mL of distilled water, stir at room temperature and add 0.5M hydrochloric acid solution to adjust the pH value to 6-7, remove excess compound shown in IV by steam distillation, suction filter, and dry the solid to obtain the compound shown in formula I (9.0g, yield 93.8%).

Embodiment 3

[0046] Slowly add the compound shown in formula II (11.5g, 60mmol) into 84g of 12% KOH aqueous solution, stir and react for 2 hours, remove part of the solvent under reduced pressure, cool, filter, and dry the dipotassium compound shown in formula III Salt (15.3 g, yield 95.1%).

[0047]Disperse the disodium salt (13.4g, 50mmol) of the compound shown in formula III in 40mL DMF, then add 5% [Bmim] BF4 ionic liquid of the dipotassium salt quality of the compound shown in III, add the compound shown in formula IV (X =I) (15.3g, 60mmol), heated to about 75-80°C and reacted for 5.0 hours. The reaction mixture was suction filtered while it was hot, and the white solid KI was removed. After the solvent DMF was evaporated, 20mL of distilled water was added, stirred at room temperature and added 0.5 M hydrochloric acid solution to adjust the pH value to 6-7, steam distillation to remove excess compound shown in IV, suction filtration, and solid drying to obtain compound shown in formul...

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Abstract

The invention discloses a method for preparing 7-methoxy -6-(3-morpholine-4-propoxy) quinazoline-4(3H)-ketone. The method comprises steps of (1) reacting the 6-hydroxy-7-methoxy quinazoline-4-ketone with inorganic base, so as to obtain a compound shown in a formula III; (2) reacting the compound shown in the formula III with a compound shown in a formula IV in the presence of ionic liquid, after the reaction, and post-processing so as to obtain the 7-methoxy-6-(3-morpholine-4-propoxy) quinazoline-4(3H)-ketone. The preparation method is simple to operate, has high reaction selectivity, and is applicable to industrial production.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to a preparation method of 7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one. Background technique [0002] The structure of 7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one is shown in the following formula (I), which is gefitinib (gefitinib, trade name One of the important intermediates of Iressa (Iressa). [0003] [0004] Gefitinib was first launched in Japan in 2002, approved by the US FDA in 2003, and launched in my country in 2005. It is the first new drug for the treatment of non-small cell lung cancer (hitting target therapy), mainly for locally advanced or metastatic disease. non-small cell lung cancer (nonsmallcelllungcancer, NSCLC). [0005] At present, the preparation method of 7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-ketone mainly contains the following kinds: [0006] The first method is to use 3-hydroxyl-4-metho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/88
CPCC07D239/88
Inventor 张洋吴建一缪程平徐永平
Owner JIAXING UNIV
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