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ChemicalBook CAS DataBase List Gefitinib
184475-35-2

Gefitinib synthesis

8synthesis methods
A mixture of 4,5-dimethoxyanthranilic acid (133) and formamide was heated to generate the cyclized quinazoline 134. The quinazoline was selectively monodemethylated with methionine in refluxing methanesulfonic acid to afford 135 in 47% yield. Compound 135 was acylated to give acetate 136, which was treated with refluxing thionyl chloride to yield chloropyrimidine 137. Chloride 137 was condensed with 3-chloro-4-fluoroaniline (138) in refluxing IPA to yield anilinoquinazoline 139 in 56% yield from 136. The acetate protecting group in compound 139 was hydrolyzed with ammonium hydroxide in methanol, and the free phenol was alkylated with 3-(4- morpholinyl)propyl chloride (140) to give gefitinib (13) in 55% yield.

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Yield:184475-35-2 99%

Reaction Conditions:

with potassium hydroxide in isopropyl alcohol at 20;

Steps:

1.e; 2.e (e) Synthesis of Gefitinib (F)

320g (0.98mol)7-methoxy-6- [3-morpholinepropoxy] -4-chloroquinazoline (E)Add to 400ml of isopropanol,Then 145 g (1 mol) of 3-chloro-4-fluoro-aniline was dissolved in 100 ml of isopropanol,It was added dropwise to the reaction solution and stirred at room temperature.After the reaction, 28 g (0.5 mol) of potassium hydroxide was added to the reaction solution, and the mixture was stirred at room temperature.Suction filtration, the filter cake was washed with an appropriate amount of isopropanol and ethanol in order, and dried under vacuum at 55 ° C to constant weight.Obtained a light beige powdery solid,That is 430 g of gefitinib, molar yield: 99%.

References:

CN110776471,2020,A Location in patent:Paragraph 0042; 0052-0053; 0054; 0064-0065

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