788136-89-0

4-((3-Chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl Acetate, is an impurity of Gefitinib (G304000), an antineoplastic.

General procedure for the synthesis of 4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol acetate from 3-chloro-4-fluoroaniline and 6-acetoxy-4-chloro-7-methoxyquinazoline: at 65°C, AuCl (4.2 g, 18 mmol), 6-acetoxy-4-chloro-7-methoxyquinazoline (12.6 g, 50 mmol) and 3-chloro-4-fluoroaniline (12.3 g, 85 mmol) were dissolved in 50 mL of methanol for substitution reaction. After completion of the reaction, the reaction mixture was filtered. The filtrate was concentrated and washed with petroleum ether to afford 16.9 g of the intermediate 4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol acetate in 93.4% yield and 99.91% purity.

[1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 2, p. 870 - 879
[2] Patent: CN105693630, 2016, A. Location in patent: Paragraph 0033
[3] Patent: CN106045980, 2016, A. Location in patent: Paragraph 0024; 0025; 0026
[4] Patent: CN108047209, 2018, A. Location in patent: Paragraph 0041; 0047; 0048
[5] Patent: WO2013/71697, 2013, A1. Location in patent: Paragraph 00195