R-afatinib

Base Information

• Chemical Name: R-afatinib
• CAS No.: 945553-91-3
• Molecular Formula: C₂₄H₂₅ClFN₅O₃
• Molecular Weight: 485.946
• Mol file: 945553-91-3.mol

Synonyms:(R,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetra- hydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino) but-2-enamide;2-Butenamide, N-[4-[(3-chloro-4-fluorophenyl)amino]-7-[[(3R)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4-(dimethylamino)-

Chemical Property of R-afatinib

Chemical Property:

• Boiling Point: 676.9±55.0 °C(Predicted)
• PKA: 11.79±0.43(Predicted)
• Density: 1.380±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

(R)-Afatinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of R-afatinib

There total 82 articles about R-afatinib 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、 -. "Arab league law for nepal preparation method of the compound". . . Retrieved 2019/04/10.
• 2、 -. "Preparation method of afatinib maleate". Paragraph 0026; 0032; 0034; 0035; 0036. . Retrieved 2019/12/25.