1680184-59-1

Basic information

• Product Name: Afatinib iMpurity
• Synonyms: Afatinib iMpurity;(2Z)-Afatinib
• CAS NO: 1680184-59-1
• Molecular Formula: C24H25ClFN5O3
• Molecular Weight: 485.94
• Mol File: 1680184-59-1.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 676.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.380±0.06 g/cm3(Predicted)
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 11.79±0.43(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: Afatinib iMpurity(CAS DataBase Reference)
• NIST Chemistry Reference: Afatinib iMpurity(1680184-59-1)
• EPA Substance Registry System: Afatinib iMpurity(1680184-59-1)

Safety Data

• Hazardous Substances Data: 1680184-59-1(Hazardous Substances Data)

Usage

Description

Afatinib iMpurity is a structural analogue of Afatinib (A355300), an aminocrotonylamino-substituted quinazoline derivative. It is primarily used for treating various types of cancer and diseases of the respiratory tract, lungs, gastrointestinal tract, bile duct, and gallbladder.

Uses

Used in Pharmaceutical Industry:
Afatinib iMpurity is used as an active pharmaceutical ingredient for the development of cancer treatments and medications targeting diseases of the respiratory tract, lungs, gastrointestinal tract, bile duct, and gallbladder. Its unique structure allows it to effectively target and inhibit specific enzymes and pathways involved in cancer growth and progression, making it a valuable compound in the fight against various malignancies.
Used in Research and Development:
Afatinib iMpurity is also utilized in research and development for the discovery of new therapeutic agents and understanding the molecular mechanisms underlying cancer and related diseases. Its structural similarity to Afatinib makes it a useful tool for studying the effects of aminocrotonylamino-substituted quinazoline derivatives on biological systems and identifying potential new drug candidates.
Used in Quality Control and Standardization:
In addition to its applications in the pharmaceutical and research industries, Afatinib iMpurity is used in quality control and standardization processes to ensure the purity, potency, and consistency of Afatinib-based medications. This helps maintain the safety and efficacy of these drugs, providing patients with reliable and effective treatment options.

Upstream product

• 618061-76-0 (S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate 
• 52334-92-6 2-(N,N-dimethylamino)ethoxide 
• 1621182-18-0 6-nitro-7-[(S)-(tetrahydrofuran-3-yl)oxy]-3,4-dihydroquinazoline-4-one 
• 314771-88-5 4-[(3-chloro-4-fluorophenyl)amino]-6-nitro-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline 
• 314771-76-1 6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline 
• 162012-67-1 N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitroquinazolin-4-amine 
• 1056149-69-9 (2E)-(N,N-dimethylamino)-2-butenoyl chloride 
• 162012-70-6 4-chloro-7-fluoro-6-nitroquinazoline 
• 86087-23-2 (S)-3-hydroxytetyrahydrofurane 

Relevant articles and documents

An alternative synthesis of the non-small cell lung carcinoma drug afatinib

Afatinib (BIBW2992) is the anticancer drug developed by Boehringer Ingelheim. This work is reporting the synthesis of the afatinib using a new route by Ullmann-Goldberg reaction from corresponding 4-anilinoquinazoline iodide as the last step in the synthesis. This route was not described previously and it could be used for synthesis of afatinib analogues.

Afatinib refined product synthetic method

The invention discloses an afatinib refined product synthetic method, and belongs to the technical field of organic synthesis. The method particularly comprises the following steps that 4-fluoro-2-aminobenzoic acid and formamidine acetate are subjected to a ring-closure reaction to synthesize a compound of the formula I; the compound of the formula I is subjected to a nitration reaction to synthesize a compound of the formul II; the compound of the formula II and 3-chloro-4-fluoroaniline are subjected to dehydration to synthesize a compound of the formula III, the compound of the formula III and 3-hydroxy-tetrahydrofuran synthesize a compound of a formula IV through a nucleophilic substitution reaction; the compound of the formula IV is reduced to generate a compound of the formula V underthe Pd/C catalysis; the compound of the formula V and crotonic acid synthesizes a compound of the formula VI through a dehydration condensation reaction; the compound of the formula VI and dimethylamine finally synthesize the compound of the formula VII, that is to say, an afatinib refined product is obtained. According to the afatinib refined product synthetic method, the reaction process condition is mild, the corrosion risk to reaction equipment is lowered, the reaction process is simplified, operation is easy, the purity of the product is high, and the yield is increased conveniently.

Arab league law for nepal preparation method of the compound

The invention provides a novel preparation method of an afatinib compound. Raw materials and reagents used in the preparation method have the advantages of low cost, stable chemical property and convenience in long-term storage and the content of an impurity cis-isomer in the prepared afatinib compound is very low.