ChemicalBook CAS DataBase List Gefitinib

Gefitinib synthesis

8synthesis methods

Product Name:Gefitinib
CAS Number:184475-35-2
Molecular formula:C22H24ClFN4O3
Molecular Weight:446.9

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.

367-21-5 Synthesis

367-21-5
525 suppliers
$5.00/25g

199327-59-8
37 suppliers
inquiry

184475-35-2
686 suppliers
$5.00/100mg

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

7-Methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one

199327-61-2
276 suppliers
$6.00/1g

367-21-5 Synthesis

367-21-5
525 suppliers
$5.00/25g

184475-35-2
686 suppliers
$5.00/100mg

References

4-Morpholinepropanol, 4-methanesulfonate

1018895-28-7
1 suppliers
inquiry

184475-71-6 Synthesis

184475-71-6
233 suppliers
$5.00/250mg

184475-35-2
686 suppliers
$5.00/100mg

References

4-Morpholinepropanol, 4-(4-methylbenzenesulfonate)

957621-67-9
0 suppliers
inquiry

184475-71-6 Synthesis

184475-71-6
233 suppliers
$5.00/250mg

184475-35-2
686 suppliers
$5.00/100mg

References

125422-83-5
66 suppliers
$165.00/0.5g

184475-71-6 Synthesis

184475-71-6
233 suppliers
$5.00/250mg

184475-35-2
686 suppliers
$5.00/100mg

References

Gefitinib Related Search:

p-Anisidine 4-Methoxyphenol PHENYL VALERATE p-Anisaldehyde Anisole Guaiacol Diphenyl ether 4-Methoxybenzyl cyanide Fluorine O-Desmorpholinopropyl Gefitinib