Gefitinib InterMediate B Chemical Properties

Melting point:

234-236 °C

Boiling point:

523.3±50.0 °C(Predicted)

Density 

1.392±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

5.40±0.30(Predicted)

Appearance

White to off-white Solid

Gefitinib InterMediate B Usage And Synthesis

Uses

4-Chloro-6-(3-chloropropoxy)-7-methoxyquinazoline is an analogue of Gefitinib, an inhibitor of EGFR with anti-tumor activity.

Synthesis

A mixture of 4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-ol (20.00 g), K2CO3 (10.37 g), KI (1.04 g), 1-bromo-3-chloropropane (7.50 mL), and DMF (150 mL) was stirred and reacted for 6 hours at 40 °C. After completion of the reaction, the reaction mixture was poured into water and the solid was collected by filtration. The filtrate was purified by silica gel column chromatography (eluent: ethyl acetate) to afford the target compound, N-(3-chloro-4-fluorophenyl)-6-(3-chloropropoxy)-7-methoxyquinazolin-4-amine, as a light yellow liquid (22.05 g, 89.00% yield). The structure of the compound was confirmed by the following spectral data: mass spectrum (ESI, positive ion mode) m/z: 396.1 ([M+H]+); 1H NMR (400 MHz, CDCl3) δ: 2.01 (m, 2H), 3.68 (t, J=4.2 Hz, 2H), 4.00 (s, 3H), 4.10 (t, J=4.2 Hz, 2H). 6.80 (s, 1H), 7.16 (s, 1H), 7.26 (s, 1H), 7.30 (s, 1H), 7.47 (s, 1H), 8.64 (s, 1H) ppm.

References

[1] Patent: WO2013/71697, 2013, A1. Location in patent: Paragraph 00197
[2] Patent: US2014/228361, 2014, A1. Location in patent: Paragraph 0277-0278
[3] Patent: US2014/206664, 2014, A1. Location in patent: Paragraph 0225; 0229
[4] Patent: EP2796451, 2014, A1. Location in patent: Paragraph 0082

Gefitinib InterMediate B(912556-91-3)Related Product Information

• Aluminum oxide
• Gefitinib InterMediate A
• 2-Amino-4-Methoxy-5-(3-Morpholinopropoxy)benzonitrile
• 3-Chloro-4-fluoroaniline
• 4-(3-Chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol
• 3,4-Dichloro Gefitinib
• Gefitinib iMpurity
• 3-DesMorpholinyl-3-hydroxyethylaMino Gefitinib
• 2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile
• 7-Methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4(3H)-one
• 3(2H)-Benzofuranone, 6-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methylene]-4-methoxy-5-methyl-
• N'-(4-Amino-2-cyanophenyl)-N,N-dimethylformamidine
• N-(3-chloro-4-fluorophenyl)-6 ,7-dimethoxyquinazolin-4-amine
• Gefitinib Impurity 14
• 4-Defluoro-4-hydroxy Gefitinib
• 3,4-Dihydro-7-methoxy-4-oxoquinazolin-6-yl acetate
• O-Desmethyl Gefitinib
• Benzaldehyde, 2-amino-4-methoxy-5-[3-(4-morpholinyl)propoxy]-