2080-75-3

Usage

Uses

Used in Pharmaceutical Industry:
5-METHOXY-2-BENZIMIDAZOLINONE is used as a synthetic intermediate for the development of a novel class of 2-3-oxospiro[isobenzofuran-1(3H),4'-piperidin]-1'-ylbenzimidazole NPY Y5 receptor antagonists. These antagonists have potential applications in treating various medical conditions by modulating the activity of the NPY Y5 receptor.
Used in Pharmaceutical Impurity:
5-METHOXY-2-BENZIMIDAZOLINONE is also used as an impurity in Esomeprazole, a gastric proton-pump inhibitor. Its presence in Esomeprazole is important for quality control and ensuring the safety and efficacy of the medication.

InChI:InChI=1/C8H8N2O2/c1-12-5-2-3-6-7(4-5)10-8(11)9-6/h2-4H,1H3,(H2,9,10,11)

Upstream product

• 530-62-1 1,1'-carbonyldiimidazole 
• 102-51-2 4-methoxy-1,2-phenylenediamine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 73590-58-6 omeprazole 
• 96-96-8 4-methoxy-2-nitroaniline 
• 57-13-6 urea 
• 124-38-9 carbon dioxide 
• 3360-81-4 N-(4-methoxy-2-nitrophenyl)-4-methylbenzenesulfonamide 
• 1150-26-1 N-(4-Methoxy-phenyl)-4-methyl-benzenesulfonamide 
• 104-94-9 4-methoxy-aniline 
• 27185-61-1 N-(2-amino-4-methoxyphenyl)-4-methylbenzenesulfonamide 
• 623-49-4 ethyl cyanoformate 
• 1329028-11-6 C₁₄H₁₆N₂O₆ 
• 213118-56-0 (2-amino-4-methoxyphenyl)carbamate tert-butyl ester 

Downstream Products

• 64107-38-6 5-methoxy-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one 
• 15965-54-5 2-chloro-5-methoxy-1H-1,3-benzimidazole 
• 1354030-44-6 5-(3-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)propoxy)-1H-benzo[d]imidazol-2(3H)-one 
• 1354030-54-8 5-(4-(4-(2,3-dichlorophenyl)piperidin-1-yl)butoxy)-1H-benzo[d]imidazol-2(3H)-one 
• 1354030-70-8 5-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propoxy)-1H-benzo[d]imidazol-2(3H)-one 
• 1354031-65-4 5-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-1H-benzo[d]imidazol-2(3H)-one 

Relevant academic research and scientific papers

Synthesis, radical scavenging activity and structure-activity relationship of uric acid analogs

Uric acid (UA) is known to play an important role as an endogenous antioxidant. However, its insolubility in the serum is a risk for hyperuricemia. We assume that UA is an equivalent to hydroquinone or p-aminophenol, which can be oxidized to quinone/quinoimine and thus acts as a radical scavenger. Based on this hypothesis, a series of UA analogs was designed and synthesized. In the chemical radical scavenging assay, active compounds were considered as hydroquinone or p-aminophenol equivalents. A highly functionalized UA structure is not essential to have radical scavenging activity. Potent active 5-hydroxyindolinones (1a, 2a, and 3a) showed sufficient activity with high solubility and low cytotoxicity.

Identification of intermediate compounds and photodegradation mechanisms of omeprazole under the system UV/O2

The photodegradation of the proton pump inhibitor omeprazole (OME) in aqueous media with the system UV/O2 is presented. The photodegradation rate was assessed by HPLC and UV-vis spectroscopy, while the mineralization rate was obtained by TOC measurements. Degradation products were investigated by IR spectroscopy and GC-MS analysis. UV-vis absorbance and HPLC results indicated that OME is completely degraded within 3?minutes of irradiation. TOC analysis indicated that intermediates compounds are relatively easy to mineralize since 80% mineralization is achieved within 2?hours. IR studies demonstrated a rapid oxidation of OME leading to the formation of amines and both sulfonic and carboxylic acids. GC-MS data indicated that the initial photoproducts are derivatives of both benzimidazole and pyridine produced after the photochemical cleavage of the C–S bond. Plausible mechanisms for the direct and indirect degradation of OME are given. In the photochemical degradation of OME, many intermediate compounds are actually generated. Several of them were generated from hydroxyl radical reactions, but some of them resulted from rearrangements, reductive reactions, and through the formation of highly reactive intermediates such as pseudo carbene, thiooxirane, and sulfenamide.

NOVEL COMPOUNDS AND THEIR USES AS THYROID HORMONE RECEPTOR AGONISTS

A compound of formula (I) or (Ia), or a tautomer or a pharmaceutically acceptable salt thereof is provided. Compounds of formula (II) to (V), or a tautomer or a pharmaceutically acceptable salt thereof are also provided. These compounds and the pharmaceutical compositions containing them are useful for the treatment of diseases such as obesity, hyperlipidemia, hypercholesterolemia and diabetes and other related disorders and diseases, and may be useful for other diseases such as NASH, atherosclerosis, cardiovascular diseases, hypothyroidism, thyroid cancer and other disorders and diseases related thereto． (I), (Ia)

Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source

A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.

Azole-Anion-Based Aprotic Ionic Liquids: Functional Solvents for Atmospheric CO2 Transformation into Various Heterocyclic Compounds

The chemical transformation of atmospheric CO2 is of great significance yet still poses a great challenge. Herein, azole-anion-based aprotic ionic liquids (ILs) were synthesized by the deprotonation of weak proton donors (e.g., 2-methylimidazole, 4-methylimidazole, and 2,4-dimethylimidazole) with tetrabutylphosphonium hydroxide, [Bu4P][OH]. We found that these ILs, such as [Bu4P][2-MIm], could activate atmospheric CO2 through the formation of carbamates. The resultant carbamate intermediates could further react with various types of substrate, including propargylic alcohols, 2-aminobenzonitriles, ortho-phenylenediamines, and 2-aminothiophenol, thereby producing α-alkylidene cyclic carbonates, quinazoline-2,4(1 H,3 H)-diones, benzimidazolones, and benzothiazoline, respectively, in moderate-to-good yields. Thus, we have achieved the transformation of CO2 at atmospheric pressure, and we expect this method to open up new routes for the synthesis of various oxygen-containing heterocyclic compounds under metal-free conditions.

GSK6853, a Chemical Probe for Inhibition of the BRPF1 Bromodomain

The BRPF (Bromodomain and PHD Finger-containing) protein family are important scaffolding proteins for assembly of MYST histone acetyltransferase complexes. A selective benzimidazolone BRPF1 inhibitor showing micromolar activity in a cellular target engag

Copper-catalyzed mild nitration of protected anilines

A practical copper-catalyzed direct nitration of protected anilines, by using one equivalent of nitric acid as the nitrating agent, has been developed. This procedure features mild reaction conditions, wide structural scope (with regard to both N-protecting group and arene substitution), and high functional-group tolerance. Dinitration with two equivalents of nitric acid is also feasible. Practical and reliable: A Cu-catalyzed selective nitration of para- and ortho-substituted aniline derivatives by using one equivalent of HNO3 has been developed that produces water as the only stoichiometric byproduct (see scheme; PG=protecting group). This method is compatible with strongly electron-deficient substrates, enabling dinitration (by using 2.0 equiv of HNO3). This method allows for a rapid access to relevant nitrogen-containing heterocyclic architectures.

FUNCTIONALLY SELECTIVE LIGANDS OF DOPAMINE D2 RECEPTORS

The present invention relates to novel functionally selective ligands of dopamine D2 receptors, including agonists, antagonists, and inverse agonists. The invention further relates to the use of these compounds for treating central nervous system disorders related to D2 receptors.

Synthesis of benzimidazolones, benzooxazolones, 2-amino-benzothiazoles from ethyl cyanoformate and o-phenylene Diamines, o-aminophenols, oaminothiophenols Promoted by Lithium Bromide ;

The lithium bromide mediated condensation of 1-amino-2-heteroaryl substrates with ethyl cyanoformate, to obtain versatile alkylcarbamate protected benzoheteroazolones was studied. This unprecedented reaction could be used to furnish different azolones like 2-benzimidazolones, 2-benooxazolones and 2-amino-thiazoles in good yields. 2011 Bentham Science Publishers Ltd.

4-(2-Pyridyl)piperazine-1-benzimidazoles as potent TRPV1 antagonists

A series of 4-(2-pyridyl)piperazine-1-benzimidazole analogues based on compound 1 was synthesized and evaluated for TRPV1 antagonist activity in capsaicin-induced (CAP) and pH 5.5-induced (pH) FLIPR assays in a human TRPV1-expressing HEK293 cell line. Potent TRPV1 antagonists were identified through SAR studies. From these studies, several antagonists were found, with IC50 values ranging from 32 nM to ～5000 nM. Among these, 11 [IC50 = 90 nM (CAP) and 104 nM (pH)] was further evaluated and found to be orally available in rats (F% = 19.7).