70254-74-9

Upstream product

• 611-21-2 N,2-dimethylaniline 
• 18102-29-9 2-methyl-6-nitroanisole 
• 74-89-5 methylamine 
• 2145-35-9 2-methyl-6-nitrotrifluoroacetanilide 
• 77-78-1 dimethyl sulfate 
• 553-90-2 Dimethyl oxalate 
• 570-24-1 2-Methyl-6-nitroaniline 
• 437-86-5 2-fluoro-3-nitrotoluene 
• 3970-40-9 2-chloro-3-nitrotoluene 
• 7664-93-9 sulfuric acid 
• 156461-85-7 N-methyl-N-nitro-o-toluidine 
• 64-19-7 acetic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 945021-49-8 C₉H₁₁N₃ 
• 73902-65-5 N₁,6-dimethylbenzene-1,2-diamine 
• 17583-45-8 1,7-dimethyl-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes

CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.

Discovery of 2-iminobenzimidazoles as potent hepatitis C virus inhibitors with a novel mechanism of action

In this report we describe 2-iminobenzimidazole (IBI) analogs, identified during the course of a phenotypic high-throughput screening campaign, as novel hepatitis C virus (HCV) inhibitors. A series of IBI derivatives was synthesized and evaluated for their inhibitory activity against infectious HCV. Among the IBIs derivatives studied in this work, we identified promising compounds with high antiviral efficacy, high selectivity index and good microsomal stability. Noteworthy, the IBI series exhibited inhibitory activity on early and late steps of the viral cycle, but not in the HCV replicon system demonstrating a mechanism of action distinct from clinical-stage and approved anti-HCV drugs. Overall, our results suggest that IBIs are predestinated for further exploration as lead compounds for novel HCV interventions.

Bicyclic Benzimidazole Compounds and Their Use as Metabotropic Glutamate Receptor Potentiators

Compounds of Formula I: wherein A, B, D, L, R1, R2, R3, R4, m, and n are as defined for Formula I in the description. The invention also relates to processes for the preparation of the compounds and to new intermediates employed in the preparation, pharmaceutical compositions containing the compounds, and to the use of the compounds in therapy.

Discovery of small molecule benzimidazole antagonists of the chemokine receptor CXCR3

High-throughput screening identified a low molecular weight antagonist of CXCR3 displaying micromolar activity in a membrane filtration-binding assay. Systematic modification of the benzimidazole core and tethered acetophenone moiety established tractable SAR of analogs with improved physicochemical properties and sub-micromolar activity across both human and murine receptors.

2-IMINO-BENZIMIDAZOLES

Novel compounds of Formula (I) or pharmaceutically acceptable salts, prodrugs and biologically active metabolites thereof of Formula (I), wherein the substituents are as defined herein, which are useful as therapeutic agents.

A 'one-pot' phase transfer alkylation/hydrolysis of o-nitrotrifluoroacetanilides. A convenient route to N-alkyl o-phenylenediamines

A variety of o-nitrotrifluoroacetanilides undergo a one-pot alkylation/hydrolysis to give N-alkyl o-nitroanilines in 40-94% yield. Dimethylsulfate, benzyl bromide and 1-bromo-propane were used as the electrophiles.

Synthesis of 1-Alkoxy-2-Alkyl-Benzimidazoles from 2-Nitroanilines via Tandem N-Alkylation-Cyclization-O-Alkylation

Substituted 2-nitroanilines react with benzylic, allyl and alkyl halides to give 2-aryl-1-benzyloxy-, 1-allyloxy-2-vinyl- and 1-alkoxy-2-alkyl-benzimidazoles, in a one-pot cascade process involving 1-alkylation-cyclization-O-alkylation. 2-Aryl-1-benzyloxy- and 1-allyloxy-2-vinyl- derivatives are obtained in high yields (79-98percent), while with simple alkyl halides, yields of the benzimidazoles are substrate dependent.An X-ray crystal structure of 2,4-dimethyl-1-ethoxybenzimidazole is presented.