77278-62-7

Usage

Physical form

white solid substance

Molecular weight

294.36 g/mol

Use

in pharmaceutical research and as an intermediate in the synthesis of various pharmaceutical compounds

Value

unique molecular structure and properties make it valuable in the development of potential drug candidates and in medicinal chemistry research.

Upstream product

• 109-09-1 2-chloropyridine 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 34803-66-2 1-(2-pyridyl)piperazine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 253175-46-1 3,3-dimethyl-1-piperazin-1-yl-butan-1-one 
• 110-86-1 pyridine 
• 77278-40-1 tert-butyl 4-(benzoyloxy)piperazine-1-carboxylate 
• 109-04-6 2-bromo-pyridine 

Downstream Products

• 497915-42-1 4-(5-iodopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester 
• 34803-66-2 1-(2-pyridyl)piperazine 
• 1268865-67-3 methyl 3-(4-fluorophenyl)-2-(4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylate 
• 1268862-77-6 3-(4-fluorophenyl)-2-(4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylic acid 
• 1268865-14-0 methyl 2-phenyl-3-(4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylate 
• 1268862-26-5 2-phenyl-3-(4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylic acid 
• 52266-53-2 1-(pyridin-2-yl)-piperazine hydrochloride 

Relevant academic research and scientific papers

Highly Selective Sub-Nanomolar Cathepsin S Inhibitors by Merging Fragment Binders with Nitrile Inhibitors

Pharmacological inhibition of cathepsin S (CatS) allows for a specific modulation of the adaptive immune system and many major diseases. Here, we used NMR fragment screening and crystal structure-aided merging to synthesize novel, highly selective CatS inhibitors with picomolar enzymatic Ki values and nanomolar functional activity in human Raji cells. Noncovalent fragment hits revealed binding hotspots, while the covalent inhibitor structure-activity relationship enabled efficient potency optimization.

Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications

C-N cross-coupling is one of the most valuable and widespread transformations in organic synthesis. Largely dominated by Pd- and Cu-based catalytic systems, it has proven to be a staple transformation for those in both academia and industry. The current study presents the development and mechanistic understanding of an electrochemically driven, Ni-catalyzed method for achieving this reaction of high strategic importance. Through a series of electrochemical, computational, kinetic, and empirical experiments, the key mechanistic features of this reaction have been unraveled, leading to a second generation set of conditions that is applicable to a broad range of aryl halides and amine nucleophiles including complex examples on oligopeptides, medicinally relevant heterocycles, natural products, and sugars. Full disclosure of the current limitations and procedures for both batch and flow scale-ups (100 g) are also described.

POLY-ADP RIBOSE POLYMERASE (PARP) INHIBITORS

The present invention is related to a pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and a compound represented by the following structural formula: The present invention is also related a method of treating a subject with a disease which can be ameliorated by inhibition of poly(ADP-ribose)polymerase (PARP). The definitions of the variables are provided herein.

Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation

Arene amination is achieved by site-selective C-H zincation followed by copper-catalyzed coupling with O-benzoylhydroxylamines under mild conditions. Key to this success is ortho-zincation mediated by lithium amidodiethylzincate base that is effective for a wide range of arenes, including nonactivated arenes bearing simple functionalities such as fluoride, chloride, ester, amide, ether, nitrile, and trifluoromethyl groups as well as heteroarenes including indole, thiophene, pyridine, and isoquinoline. An analogous C-H azidation is also accomplished using azidoiodinane for direct introduction of a useful azide group onto a broad scope of arenes and heteroarenes. These new transformations offer rapid access to valuable and diverse chemical space of aminoarenes. Their broad applications in organic synthesis and drug discovery are demonstrated in the synthesis of novel analogues of natural product (-)-nicotine and antidepressant sertraline by late-stage amination and azidation reactions.

A tuned bicyclic proazaphosphatrane for catalytically enhanced n-arylation reactions with aryl chlorides

The N-arylation of various amines with aryl chlorides proceeded in good-to-excellent yields in the presence of P[N{(p-NMe2)C6H4CH2}CH2CH2]3N (1e, a new electron-rich proazaphosphatrane ligand) and small amounts of Pd2(dba)3 (dba = dibenzylideneacetone). This catalytic system was also very effective for the synthesis of carbazoles. An efficient palladium-catalyzed N-arylation reaction of amines under mild conditions with a tuned bicyclic proazaphosphatrane has been developed.

"Throwing away" a different ancillary ligand to enhance the catalytic activity at room temperature

A considerable effort in ligand design for catalysis in recent years has led to remarkable achievements in cross-coupling reactions. In this work, we show that a careful selection of the ancillary ligands that complete the catalyst/precatalyst can provide an extra level of performance. Low loadings of [(IPr)PdCl2(TEA)] {IPr = 1,3-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene, TEA = triethylamine} catalyze the Buchwald-Hartwig amination reactions of aryl chlorides at room temperature in excellent yields, without the need for an inert atmosphere to set up or perform the reactions.

"throwing away" a different ancillary ligand to enhance the catalytic activity at room temperature

A considerable effort in ligand design for catalysis in recent years has led to remarkable achievements in cross-coupling reactions. In this work, we show that a careful selection of the ancillary ligands that complete the catalyst/precatalyst can provide

Solvent free N-Boc protection of amines using amberlystr a 21 solid base resin as a reusable heterogeneous catalyst

An efficient, environmentally benign, highly facile and convenient synthetic protocol for the selective t-butyl carboxylation of aliphatic, aromatic and heterocyclic amines using AmberlystR A 21 catalyst; a mild basic solid resin under solvent free conditions is reported. This method explores several advantages such as reusability of the heterogeneous catalyst, cleaner reaction profile, mild and solvent free system, short reaction time, operational simplicity, high conversions , excellent product yields and low cost of the catalyst. Furthermore since the catalyst is mild basic, decomposition of the carbamate formed is not observed if the reaction is continued for prolonged time as in the case of Lewis acid catalyzed N-Boc protection. This makes the present protocol a useful and attractive for N-Boc protection of amines.

THERAPEUTICALLY ACTIVE COMPOUNDS FOR USE IN THE TREATMENT OF CANCER CHARACTERIZED AS HAVING AN IDH MUTATION

Compounds and compositions comprising compounds useful in the treatment of cancer are described herein. The compounds and compositions can be used to modulate an isocitrate dehydrogenase (IDH) mutant (e.g., IDHIm or IDH2m) having alpha hydroxyl neoactivity

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.