381233-78-9

Basic information

• Product Name: 5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE
• Synonyms: [2,3'-BIPYRIDIN]-6'(1'H)-ONE;5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE;5-(Pyridin-2-yl)-2(1H)-pyridone;5-(Pyridin-2-yl)-1,2-dihydropyridin-2-one;5-(Pyridin-2-yl)pyridin-2(1H)-one;5-(2-Pyridyl)pyridin-2(1H)-one;5-pyridin-2-yl-1H-pyridin-2-one;5-(2-PYRIDYL)-2-PYRIDONE
• CAS NO: 381233-78-9
• Molecular Formula: C₁₀H₈N₂O
• Molecular Weight: 172.19
• Mol File: 381233-78-9.mol

Chemical Properties

• Boiling Point: 434.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.221±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 10.85±0.10(Predicted)
• CAS DataBase Reference: 5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE(381233-78-9)
• EPA Substance Registry System: 5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE(381233-78-9)

Safety Data

• Hazardous Substances Data: 381233-78-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE is used as a key intermediate in the synthesis of AMPA receptor antagonists for the treatment of neurological diseases. These diseases are characterized by the dysfunction of glutamatergic neurotransmission, which can lead to a range of neurological disorders. By acting as an antagonist to the AMPA receptor, this compound can help regulate the excitatory neurotransmission and alleviate the symptoms associated with these conditions.

InChI:InChI=1S/C10H8N2O/c13-10-5-4-8(7-12-10)9-3-1-2-6-11-9/h1-7H,(H,12,13)

Upstream product

• 381725-49-1 2-methoxy-5-(pyridin-2-yl)pyridine 
• 71-36-3 butan-1-ol 
• 93297-75-7 2-chloro-5-(2'-pyridyl)pyridine 
• 1124-29-4 1-(6-hydroxypyridin-3-yl)ethanone 
• 21966-78-9 1,3-dimethyl-2-oxo-2,3-dihydropyrimidin-1-ium chloride 
• 342618-54-6 6'-bromo-[2,3']bipyridinyl 
• 109-04-6 2-bromo-pyridine 
• 1054483-78-1 2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 624-28-2 2,5-dibromopyridine 
• 13472-85-0 2-methoxy-5-bromopyridine 
• 17997-47-6 2-tri-n-butylstannylpyridine 
• 163105-89-3 2-methoxy-pyridine-5-boronic acid 
• 197958-29-5 pyridin-2-ylboronic acid 
• 58757-38-3 6-Chloronicotinoyl chloride 

Downstream Products

• 381725-50-4 1-phenyl-5-(pyridin-2-yl)-2(1H)-pyridone 
• 1338225-44-7 C₁₈H₁₆N₂S 
• 381248-06-2 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one 
• 380917-97-5 [14C]-Perampanel 
• 543699-66-7 3-bromo-1-(3-methoxyphenyl)-5-(2-pyridyl)-1,2-dihydropyridin-2-one 
• 1415212-88-2 C₁₇H₁₃BrN₂O₂ 
• 1415212-91-7 C₁₇H₁₀BrN₃O 
• 380918-50-3 C₂₃H₁₈N₂O 
• 381233-79-0 3-bromo-5-(2-pyridyl)-1,2-dihydropyridin-2-one 
• 380919-26-6 3-(2-Trifluoromethylphenyl)-5-(2-pyridyl)-1-(3-pyridyl) 1,2-dihydropyridin-2-one 

Relevant articles and documents

pyrrole logical sequence handkerchief nai intermediate preparation method (by machine translation)

The invention relates to a simple operation, raw materials are easy, and the production cost is low, the quality of the product is good and is suitable for the industrial production of the intermediate pyrrole logical sequence handkerchief nai 5 - (pyridine - 2 - yl) - 2 (1H) - pyridone of the preparation method. (by machine translation)

PROCESS FOR THE PREPARATION OF PERAMPANEL

The present invention relates to processes for the preparation of perampanel and its intermediates.

Development of Novel PET Probes for Central 2-Amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic Acid Receptors

We document the development of PET probes for central AMPA receptors and their application to in vivo animal imaging. An initial screening of perampanel derivatives was performed to identify probe candidates. Despite the high autoradiographic contrast yie

PYRIDAZINE DERIVATIVES AS EAAT2 ACTIVATORS

Pyridazine derivatives that activate the excitatory amino acid transporter 2 (EAAT2), and methods of use thereof for treating or preventing diseases, disorders, and conditions associated with glutamate excitotoxicity.

METHODS FOR PREPARING INTERMEDIATES OF PERAMPANEL

Methods for the synthesis of 2-alkoxy-5-(pyridin-2-yl)pyridine of formula I or salts thereof are provided.

Process for the preparation of 2-alkoxy-5-(pyridin-2-yl)pyridine, an intermediate of perampanel

The present invention relates to a process for synthesising 2-alkoxy-5-(pyridin-2-yl)pyridine which is an intermediate of the synthesis of the active substance Perampenel.

A practical, laboratory-scale synthesis of Perampanel

The orally active, noncompetitive, selective AMPA receptor antagonist Perampanel, 2-[1,6-dihydro-6-oxo-1-phenyl-(2,3-bipyridin)-5-yl]benzonitrile, has been prepared from readily available, relatively inexpensive starting materials. The synthesis was carried out on a laboratory scale with no specialized equipment, and involved only two chromatographic purifications. Georg Thieme Verlag Stuttgart. New York.

Discovery of 2-(2-Oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl) benzonitrile (Perampanel): A novel, noncompetitive α-amino-3-hydroxy-5- methyl-4-isoxazolepropanoic acid (AMPA) receptor antagonist

Dysfunction of glutamatergic neurotransmission has been implicated in the pathogenesis of epilepsy and numerous other neurological diseases. Here we describe the discovery of a series of 1,3,5-triaryl-1H-pyridin-2-one derivatives as noncompetitive antagonists of AMPA-type ionotropic glutamate receptors. The structure-activity relationships for this series of compounds were investigated by manipulating individual aromatic rings located at positions 1, 3, and 5 of the pyridone ring. This culminated in the discovery of 2-(2-oxo-1-phenyl-5- pyridin-2-yl-1,2-dihydropyridin-3-yl)benzonitrile (perampanel, 6), a novel, noncompetitive AMPA receptor antagonist that showed potent activity in an in vitro AMPA-induced Ca2+ influx assay (IC50 = 60 nM) and in an in vivo AMPA-induced seizure model (minimum effective dose of 2 mg/kg po). Perampanel is currently in regulatory submission for partial-onset seizures associated with epilepsy.

Structure-activity relationship study of pyridazine derivatives as glutamate transporter EAAT2 activators

Excitatory amino acid transporter 2 (EAAT2) is the major glutamate transporter and functions to remove glutamate from synapses. A thiopyridazine derivative has been found to increase EAAT2 protein levels in astrocytes. A structure-activity relationship study revealed that several components of the molecule were required for activity, such as the thioether and pyridazine. Modification of the benzylthioether resulted in several derivatives (7-13, 7-15 and 7-17) that enhanced EAAT2 levels by >6-fold at concentrations 50 of 0.5 μM.

PRODUCTION PROCESS OF 2,3'-BIPYRIDYL-6'-ONE

A production process where 2,3′-bipyridyl-6′-one can be produced in high purity at low cost on an industrial scale without using an expensive catalyst or special equipment is provided. A process for producing 2,3′-bipyridyl-6′-one comprises reacting an acetylpyridine derivative with at least one of compounds represented by formulae (II) to (V) to synthesize a bipyridine derivative and hydrolyzing the bipyridine derivative by one-pot preparation. In formulae (II) to (V), each of R2 to R8, X and Y represents a given group.