Afatinib iMpurity

Base Information

• Chemical Name: Afatinib iMpurity
• CAS No.: 1680184-59-1
• Molecular Formula: C₂₄H₂₅ClFN₅O₃
• Molecular Weight: 485.946
• Mol file: 1680184-59-1.mol

Synonyms:

Chemical Property of Afatinib iMpurity

Chemical Property:

• Melting Point: >134°C (dec.)
• Boiling Point: 676.9±55.0 °C(Predicted)
• PKA: 11.79±0.43(Predicted)
• Density: 1.380±0.06 g/cm3(Predicted)
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

(2Z)-Afatinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (2Z)-Afatinib is a structural analogue of Afatinib (A355300), an aminocrotonylamino-substituted quinazoline derivative used for treating cancer and diseases of the respiratory tract, lungs, gastrointestinal tract, bile duct, and gallbladder.

Technology Process of Afatinib iMpurity

There total 80 articles about Afatinib iMpurity which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline (314771-76-1,402855-03-2) + (E)-4-(dimethylamino)-2-butenoic acid methyl ester (212776-19-7) → afatinib (850140-72-6,1680184-59-1,945553-91-3,439081-17-1,439081-18-2)

Guidance literature:

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline; With trimethylaluminum; In hexane; dichloromethane; at 20 ℃; for 2h;

(E)-4-(dimethylamino)-2-butenoic acid methyl ester; In hexane; dichloromethane; at 60 ℃; for 5h; Solvent;

Reference yield: 97.7%

(S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate (618061-76-0) + dimethylaminoacetaldehyde diethyl acetal (3616-56-6) → afatinib (850140-72-6,1680184-59-1,945553-91-3,439081-17-1,439081-18-2)

Guidance literature:

dimethylaminoacetaldehyde diethyl acetal; With hydrogenchloride; In water; at 20 - 30 ℃; Inert atmosphere;

(S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate; With lithium chloride; potassium hydroxide; In tetrahydrofuran; at -15 - 20 ℃; for 2.5h; Product distribution / selectivity; Inert atmosphere;

Reference yield: 97.5%

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline (314771-76-1,402855-03-2) + trans-4-dimethylamino crotonic acid chloride hydrochloride salt (1055943-40-2) → afatinib (850140-72-6,1680184-59-1,945553-91-3,439081-17-1,439081-18-2)

Guidance literature:

In tetrahydrofuran; at 0 - 5 ℃;

upstream raw materials:

4-cyanophenol

4-hydroxy-3-nitrobenzonitrile

3-chloro-4-fluorophenylamine

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline

Refernces

• 1、 -. "Preparation method of quinazolinyl butylene amide compound". Paragraph 0045-0049; 0053-0057; 0060-0064; 0067-0071; .... . Retrieved 2021/07/17.
• 2、 -. "Preparation method of afatinib maleate". Paragraph 0026; 0032; 0034; 0035; 0036. . Retrieved 2019/12/25.