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

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

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

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• 3272-08-0 4-hydroxy-3-nitrobenzonitrile 
• 367-21-5 3-chloro-4-fluorophenylamine 
• 314771-76-1 6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline 
• 52334-92-6 2-(N,N-dimethylamino)ethoxide 
• 86087-23-2 (S)-3-hydroxytetyrahydrofurane 
• 162012-67-1 N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitroquinazolin-4-amine 
• 1637254-93-3 6-(4-bromocrotamido)-7-((S)-tetrahydrofuran-3-yloxy)-N-(3-chloro-4-fluorophenyl)quinazolin-4-amine 
• 124-40-3 dimethyl amine 
• 16499-57-3 7-fluoro-3,4-dihydroquinazolin-4-one 

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.

Preparation method of quinazolinyl butylene amide compound

The invention discloses a preparation method of a quinazolinyl butylene amide compound, which effectively reduces the generation of impurities in the synthesis process by selecting a proper mixed alkali system and using a mixture of 1, 5-diaza-bicyclo [4.3. 0] nonyl-5-ene and potassium hydroxide, avoids the additional generation of degraded impurities in the medicine storage process, and accurate control over impurity generation and degradation is achieved.

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.

Preparation method of afatinib maleate

The invention belongs to the technical field of medicine preparation, and particularly relates to a preparation method of afatinib maleate. The preparation method of the afatinib maleate comprises thefollowing steps: reacting N4-(3-chloro-4-fluorophenyl)-

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.

PROCESS FOR THE PREPARATION OF N-[4-[(3-CHLORO-4-FLUORO PHENYL) AMINO]-7-[[(3s-TETRAHYDRO-3-FURANYL]OXY]-6-QUINAZOLINYL]-4-(DIMETHYL AMINO)-(2E)-2-BUTENAMIDE (2Z)-2-BUTENEDIOATE (1 :2) AND ITS POLYMORPHS THEREOF

The present invention relates to an improved process for the preparation of N-[4-[(3-chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4-(dimethyl amino)-(2E)-2-butenamide (2Z)-2-butenedioate (1:2) represented by the following structural formula:

Synthesis method of afatinib

The invention discloses a synthesis method of afatinib. The synthesis method comprises the steps as follows: (a), a compound shown in a formula (4) reacts with a compound shown in a formula (5) to produce a compound shown in a formula (3); (b), the compound shown in the formula (3) produces a compound shown in a formula (2) in an organic solvent under the action of a bromination reagent; (c) the compound shown in the formula (2) reacts with dimethylamine to produce a compound shown in a formula (1). The synthesis reaction of the route is suitable for mass production, double bond cis-trans isomerism is not involved, and the product purity is very high. The reaction route is shown in the description.

Preparation method of afatinib and maleate thereof

The invention belongs to the technical field of synthesis of compounds, and relates to a preparation method of afatinib and maleate thereof. The preparation method comprises the following steps: in the presence of a first organic solvent, adopting N-4-[(3-chloro-4-fluorophenyl)]-7-{[(3S)-tetrahydrofuran-3-group]oxo}-4,6-quinazoline diamine as a raw material to have the acylation reaction with (E)-4-dimethyl amino crotonate hydrochloride to obtain an acylation reaction solution under the effect of thionyl chloride, water and alkaline water are added into the acylation reaction solution, the water phase is extracted by virtue of butyl acetate, an organic phase is collected, after the organic phase is washed, the organic phase is directly stirred and precipitated to obtain an afatinib crude product, then the afatinib crude product is refined to obtain a competitive product, and the competitive product reacts with maleic acid to obtain maleic acid afatinib. The method has the characteristics of being high in product yield, high in purity, low in impurity content, mild in reaction conditions, simple in operation, suitable for industrialized production and the like.

A arab league law for nepal and its preparation method and application

The present invention provides afatinib, a preparation method therefor and an application thereof. The method comprises: by taking carbon tetrabromide and an organophosphorus compound as a condensation reagent, taking a dimethyl amino crotonic acid and/or dimethyl amino crotonic acid salt and N4-(3-chlorine-4-fluorine-phenyl)-7-(( S )-tetrahydrofuran-3-yloxy) quinazoline-4, 6-diamine as raw materials, performing a condensation reaction to generate the afatinib. According to the preparation method provided by the present invention, the carbon tetrabromide and the organophosphorus compound are taken as the condensation reagent, and the afatinib can be obtained by virtue of one-step condensation reaction. The process is simple, and during the process of preparing the afatinib, a selection range of the condensation reagent is expanded; and the reaction yield can be higher than 90%, and the product purity is higher than 95%.