940284-98-0

Usage

Uses

Used in Pharmaceutical Research and Development:
2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE-5-BORONIC ACID PINACOL ESTER is used as a key building block for the synthesis of pharmaceuticals due to its complex structure and multiple functional groups. It aids in the creation of new drugs and biologically active molecules, enhancing the discovery and development of novel therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE-5-BORONIC ACID PINACOL ESTER is employed as a versatile intermediate for the construction of various organic compounds. Its unique reactivity allows chemists to explore new synthetic pathways and develop innovative methods for the preparation of complex organic molecules.
Used in Medicinal Chemistry:
2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE-5-BORONIC ACID PINACOL ESTER is utilized as a crucial component in medicinal chemistry for the design and synthesis of potential drug candidates. Its presence in the molecular structure can impart specific biological activities, making it an essential tool for the development of new therapeutic agents with improved efficacy and selectivity.
Used in Chemical Research:
In the realm of chemical research, 2-(4-BOC-PIPERAZIN-1-YL)PYRIMIDINE-5-BORONIC ACID PINACOL ESTER is employed as a model compound to study the reactivity and properties of boronic acid pinacol esters and other functional groups. This helps in understanding the underlying chemical principles and contributes to the advancement of chemical knowledge and technology.

Upstream product

• 374930-88-8 tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate 
• 73183-34-3 bis(pinacol)diborane 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 780705-64-8 1-piperazinecarboxylic acid 4-(2-pyrimidinyl)-, 1,1-dimethylethyl ester 

Downstream Products

• 1246372-67-7 4-{5-[2-(3,4-dimethoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-pyrimidin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester 
• 1272973-58-6 4-(5-hydroxypyrimidin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester 
• 1272972-49-2 tert-butyl 4-(5-{[4-(methylsulfonyl)benzyl]oxy}pyrimidin-2-yl)piperazine-1-carboxylate 

Relevant academic research and scientific papers

Two Ligands Transfer from Ag to Pd: En Route to (SIPr)Pd(CF2H)(X) and Its Application in One-Pot C-H Borylation/Difluoromethylation

A process for the concurrent transfer of both the NHC ligand and the difluoromethyl group from [(SIPr)Ag(CF2H)] to PdX2 (X = Cl, OAc, and OPiv) for the preparation of [(SIPr)Pd(CF2H)X] complexes is described. These complexes were air-stable and easily underwent transmetalation with aryl pinacol boronate/reductive elimination to generate ArCF2H in high yields. Based on this discovery, the first one-pot C-H borylation and difluoromethylation process for the preparation of difluoromethylated (hetero)arenes was developed.

Improvement of Aqueous Solubility of Lapatinib-Derived Analogues: Identification of a Quinolinimine Lead for Human African Trypanosomiasis Drug Development

Lapatinib, an approved epidermal growth factor receptor inhibitor, was explored as a starting point for the synthesis of new hits against Trypanosoma brucei, the causative agent of human African trypanosomiasis (HAT). Previous work culminated in 1 (NEU-1953), which was part of a series typically associated with poor aqueous solubility. In this report, we present various medicinal chemistry strategies that were used to increase the aqueous solubility and improve the physicochemical profile without sacrificing antitrypanosomal potency. To rank trypanocidal hits, a new assay (summarized in a cytocidal effective concentration (CEC50)) was established, as part of the lead selection process. Increasing the sp3 carbon content of 1 resulted in 10e (0.19 μM EC50 against T. brucei and 990 μM aqueous solubility). Further chemical exploration of 10e yielded 22a, a trypanocidal quinolinimine (EC50: 0.013 μM; aqueous solubility: 880 μM; and CEC50: 0.18 μM). Compound 22a reduced parasitemia 109 fold in trypanosome-infected mice; it is an advanced lead for HAT drug development.

A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from commercially available anthracene derivatives. The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

Iridium-catalyzed C-H borylation of heteroarenes: Scope, regioselectivity, application to late-stage functionalization, and mechanism

A study on the iridium-catalyzed C-H borylation of heteroarenes is reported. Several heteroarenes containing multiple heteroatoms were found to be amenable to C-H borylation catalyzed by the combination of an iridium(I) precursor and tetramethylphenanthroline. The investigations of the scope of the reaction led to the development of powerful rules for predicting the regioselectivity of borylation, foremost of which is that borylation occurs distal to nitrogen atoms. One-pot functionalizations are reported of the heteroaryl boronate esters formed in situ, demonstrating the usefulness of the reported methodology for the synthesis of complex heteroaryl structures. Application of this methodology to the synthesis and late-stage functionalization of biologically active compounds is also demonstrated. Mechanistic studies show that basic heteroarenes can bind to the catalyst and alter the resting state from the olefin-bound complex observed during arene borylation to a species containing a bound heteroarene, leading to catalyst deactivation. Studies on the origins of the observed regioselectivity show that borylation occurs distal to N-H bonds due to rapid N-H borylation, creating an unfavorable steric environment for borylation adjacent to these bonds. Computational studies and mechanistic studies show that the lack of observable borylation of C-H bonds adjacent to basic nitrogen is not the result of coordination to a bulky Lewis acid prior to C-H activation, but the combination of a higher-energy pathway for the borylation of these bonds relative to other C-H bonds and the instability of the products formed from borylation adjacent to basic nitrogen.

Use of small-molecule crystal structures to address solubility in a novel series of g protein coupled receptor 119 agonists: Optimization of a lead and in vivo evaluation

G protein coupled receptor 119 (GPR119) is viewed as an attractive target for the treatment of type 2 diabetes and other elements of the metabolic syndrome. During a program toward discovering agonists of GPR119, we herein describe optimization of an initial lead compound, 2, into a development candidate, 42. A key challenge in this program of work was the insolubility of the lead compound. Small-molecule crystallography was utilized to understand the intermolecular interactions in the solid state and resulted in a switch from an aryl sulphone to a 3-cyanopyridyl motif. The compound was shown to be effective in wild-type but not knockout animals, confirming that the biological effects were due to GPR119 agonism.

BENZOTHIAZOLES AND AZA-ANALOGUES THEREOF USE AS ANTIBACTERIAL AGENTS

The present invention provides Gyrase B and/or Topoisomerase IV par E inhibitors, which can be used as antibacterial agents. Compounds disclosed herein can be used for treating or preventing conditions caused by or contributed by gram positive, gram negative and anaerobic bacteria, more particularly against, for example, Staphylococci, Streptococci, Enterococci, Haemophilus, Pseudomonas spp., Acenetobacter spp., Moraxalla spp., Chlamydia spp., Mycoplasma spp., Legionella spp., Ktycobacterium spp., Helicobacter, Clostridium spp., Bacteroides spp., Coryne bacterium, Bacillus spp., Enterobactericeae,' (E.coli, Klebsiella spp., Proteus spp.,etc. ) or any combination thereof Also provided, are processes for preparing compounds disclosed herein, pharmaceutical compositions containing compounds disclosed herein, and methods of treating bacterial infections. (Formula)

AROMATIC COMPOUND

An aromatic compound represented by the following formula or a pharmaceutically acceptable salt thereof: , wherein ring A is a heterocyclic ring, ring B is a carbocyclic ring, a heterocyclic ring etc., G1, G2, G3, G4 and G5 are CH or N, X is -NH-, -O-, -CH2-, etc., Y is - CH2-,-CO-,-SO2- etc., Z is a single bond, -CO-, -SO2-, -NH-, -O-, -S-, -CONH-,-SO2NH-, etc., R2 is hydrogen, alkyl, alkoxy, halogen, etc., and R3 is carbocyclic group, heterocyclic group, alkyl, etc., is useful as a controlling agent of the function of CCR4 useful for the treatment or therapy for bronchial asthma, atopic dermatitis, etc.