134485-97-5

Basic information

• Product Name: 2,4-BIS-(2-METHYL-IMIDAZOL-1-YL)-PHENYLAMINE
• Synonyms: 2,4-BIS-(2-METHYL-IMIDAZOL-1-YL)-PHENYLAMINE
• CAS NO: 134485-97-5
• Molecular Formula: C₁₄H₁₅N₅
• Molecular Weight: 253.3024
• Mol File: 134485-97-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 536.1°C at 760 mmHg
• Flash Point: 278°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 1.44E-11mmHg at 25°C
• Refractive Index: 1.679
• CAS DataBase Reference: 2,4-BIS-(2-METHYL-IMIDAZOL-1-YL)-PHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-BIS-(2-METHYL-IMIDAZOL-1-YL)-PHENYLAMINE(134485-97-5)
• EPA Substance Registry System: 2,4-BIS-(2-METHYL-IMIDAZOL-1-YL)-PHENYLAMINE(134485-97-5)

Safety Data

• Hazardous Substances Data: 134485-97-5(Hazardous Substances Data)

Usage

General Description

2,4-BIS-(2-METHYL-IMIDAZOL-1-YL)-PHENYLAMINE, also known as HMIM, is a chemical compound with the molecular formula C18H20N6. It is a member of the imidazole chemical family and is commonly used as a ligand in coordination chemistry and as a building block in organic synthesis. HMIM has been studied for its potential application in pharmaceuticals, particularly as a potential anti-cancer drug. Its unique structure and chemical properties make it useful in a variety of scientific and industrial applications. However, its potential biological and environmental impacts are still being studied.

InChI:InChI=1/C14H15N5/c1-10-16-5-7-18(10)12-3-4-13(15)14(9-12)19-8-6-17-11(19)2/h3-9H,15H2,1-2H3

Upstream product

• 446-35-5 2,4-Difluoronitrobenzene 
• 134485-96-4 1,1'-(1-nitrobenzene-2,4-diyl)bis(2-methyl-1H-imidazole) 

Relevant articles and documents

Discovery of 1-(3′-aminobenzisoxazol-5′-yl)-3-trifluoromethyl- N-[2-fluoro-4-[(2′-dimethylaminomethyl)imidazol-1-yl]phenyl] -1H-pyrazole-5-carboxyamide hydrochloride (razaxaban), a highly potent, selective, and orally bioavailable factor Xa inhibitor

Modification of a series of pyrazole factor Xa inhibitors to incorporate an aminobenzisoxazole as the P1 ligand resulted in compounds with improved selectivity for factor Xa relative to trypsin and plasma kallikrein. Further optimization of the P4 moiety led to compounds with enhanced permeability and reduced protein binding. The SAR and pharmacokinetic profile of this series of compounds is described herein. These efforts culminated in 1-(3′-aminobenzisoxazol-5′-yl)-3-trifluoromethyl-N-[2-fluoro-4- [(2′-dimethylaminomethyl)imidazol-1-yl]phenyl]-1H-pyrazole-5-carboxyamide (11d), a potent, selective, and orally bioavailable inhibitor of factor Xa. On the basis of its excellent in vitro potency and selectivity profile, high free fraction in human plasma, good oral bioavailability, and in vivo efficacy in antithrombotic models, the HCl salt of this compound was selected for clinical development as razaxaban (DPC 906, BMS-561389).