1398507-08-8

Basic information

• Product Name: 4-(4-aMino-6-chloropyriMidin-2-ylaMino)benzonitrile
• Synonyms: 4-(4-aMino-6-chloropyriMidin-2-ylaMino)benzonitrile;4-[(4-amino-6-chloro-2-pyrimidinyl)amino]benzonitrile
• CAS NO: 1398507-08-8
• Molecular Formula: C₁₁H₈ClN₅
• Molecular Weight: 245.66772
• Mol File: 1398507-08-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 4-(4-aMino-6-chloropyriMidin-2-ylaMino)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-aMino-6-chloropyriMidin-2-ylaMino)benzonitrile(1398507-08-8)
• EPA Substance Registry System: 4-(4-aMino-6-chloropyriMidin-2-ylaMino)benzonitrile(1398507-08-8)

Safety Data

• Hazardous Substances Data: 1398507-08-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-amino-6-chloropyrimidin-2-ylamino)benzonitrile is used as a key intermediate in the synthesis of various pharmaceutical drugs. Its unique chemical structure allows it to be a building block for the development of new therapeutic agents.
Used in Organic Chemistry:
In the field of organic chemistry, 4-(4-amino-6-chloropyrimidin-2-ylamino)benzonitrile is utilized as a versatile compound for the preparation of different organic compounds. Its reactivity and structural features make it a valuable component in the synthesis of complex organic molecules.
Used in Drug Development:
4-(4-amino-6-chloropyrimidin-2-ylamino)benzonitrile plays a crucial role in drug development, where it is employed to create new pharmaceutical agents with potential therapeutic benefits. Its properties enable it to be integrated into the molecular structures of drugs targeting a range of medical conditions.

Upstream product

• 5637-42-3 1-(4-cyanophenyl)guanidine 
• 1398507-07-7 4-(4-amino-6-hydroxy-pyrimidin-2-ylamino)-benzonitrile 
• 873-74-5 4-Aminobenzonitrile 
• 10132-07-7 4-amino-2,6-dichloropyrimidine 
• 104-15-4 toluene-4-sulfonic acid 

Downstream Products

• 1404118-66-6 N-[6-chloro-2-(4-cyanophenylamino)pyrimidin-4-yl]benzamide 
• 269055-15-4 etravirine 
• 1404118-67-7 N-[5-bromo-6-chloro-2-(4-cyanophenylamino)-pyrimidin-4-yl]-benzamide 
• 1404118-68-8 N-[5-bromo-6-(4-cyano-2,6-dimethylphenoxy)-2-(4-cyano-phenylamino)pyrimidin-4-yl]-benzamide 
• 1398507-09-9 4-((4-amino-5-bromo-6-chloropyrimidin-2-yl)amino)benzonitrile 

Relevant articles and documents

JAK2 JH2 Fluorescence Polarization Assay and Crystal Structures for Complexes with Three Small Molecules

A competitive fluorescence polarization (FP) assay is reported for determining binding affinities of probe molecules with the pseudokinase JAK2 JH2 allosteric site. The syntheses of the fluorescent 5 and 6 used in the assay are reported as well as Kd results for 10 compounds, including JNJ7706621, NVP-BSK805, and filgotinib (GLPG0634). X-ray crystal structures of JAK2 JH2 in complex with NVP-BSK805, filgotinib, and diaminopyrimidine 8 elucidate the binding poses.

PROCESS FOR THE PREPARATION OF ETRAVIRINE AND INTERMEDIATES IN THE SYNTHESIS THEREOF

The present invention includes compounds of Formula (1) of the following structure: or salts thereof, wherein X is a halogen or a tosyl group. Processes for preparing the compounds of Formula (1) are disclosed in the patent application. The compounds of Formula I are useful as intermediates for preparation of Etravirine. The present invention is also directed toward processes for preparing Etravirine.

PROCESS FOR THE PRODUCTION OF ETRAVIRINE

A novel process for the preparation of Etravirine comprises the condensing of ethyl cyanoacetate with N-cyanophenylguanidine to obtain an —OH compound of formula (II), which is further converted to a leaving group of formula (III). The compound of formula (III) is optionally protected and brominated to yield compound of formula (IV). The condensation of formula (IV) with 3,5-dimethyl-4-hydroxybenzonitrile yields a compound of formula (VI), and an optional deprotection of the compound of formula (VI) results in Etravirine.

NOVEL PROCESS FOR THE PREPARATION OF ETRAVIRINE

The present invention relates to a novel process for the preparation of Etravirine, comprises; condensing ethyl cyanoacetate with N-cyanophenylguanidine to obtain -OH compound of formula (II), which is further converted to a leaving group of formula (III). Compound of formula (III) is optionally protected and brominated to yield compound of formula (IV). Condensation of formula (IV) with 3,5-dimethyl-4-hydroxybenzonitrile gives formula (VI), and an optional deprotection of formula (VI) results into Etravirine. The present invention further relates to process for purifying Etravirine. The present invention also provides novel intermediates of Etravirine.