18591-57-6

Basic information

• Product Name: 5,6-DIPHENYLPYRAZIN-2-OL
• Synonyms: 5,6-DIPHENYLPYRAZIN-2-OL;5,6-diphenylpyrazin-2(1H)-one;5,6-Diphenylpyrazinol;5,6-Diphenyl-2(1H)-pyrazinone;5,6-Diphenyl-2-hydroxypyrazine;5,6-diphenyl-1H-pyrazin-2-one
• CAS NO: 18591-57-6
• Molecular Formula: C₁₆H₁₂N₂O
• Molecular Weight: 248.28
• Mol File: 18591-57-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 225-227 °C
• Boiling Point: 492.2°C at 760 mmHg
• Flash Point: 251.4°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 2.61E-10mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.55±0.60(Predicted)
• CAS DataBase Reference: 5,6-DIPHENYLPYRAZIN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIPHENYLPYRAZIN-2-OL(18591-57-6)
• EPA Substance Registry System: 5,6-DIPHENYLPYRAZIN-2-OL(18591-57-6)

Safety Data

• Hazardous Substances Data: 18591-57-6(Hazardous Substances Data)

Usage

Uses

5,6-Diphenylpyrazinol is a diphenylpyrazine derivative which belongs to a class of prostacyclin receptor agonists. It is impurity of Selexipag (S253150) that is a potential drug for the treatment of various vascular disorders such as pulmonary arterial hypertension and arteriosclerosis obliterans.

InChI:InChI=1/C16H12N2O/c19-14-11-17-15(12-7-3-1-4-8-12)16(18-14)13-9-5-2-6-10-13/h1-11H,(H,18,19)

Upstream product

• 1668-10-6 glycinamide hydrochloride 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 83520-60-9 5-Acetoxy-2,3-diphenylpyrazine 
• 134-81-6 benzil 
• 598-41-4 H-Gly-NH₂ 
• 67-56-1 methanol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 924-44-7 glyoxylic acid ethyl ester 
• 117878-22-5 [1,1':2',1''-terphenyl]-4',5'-diamine 
• 108982-09-8 2-bromo-3-methoxy-5,6-diphenyl-pyrazine 
• 34121-78-3 3-oxo-5,6-diphenyl-3,4-dihydro-pyrazine-2-carbonitrile 
• 75163-71-2 2,3-dibromo-5,6-diphenylpyrazine 
• 61578-13-0 2,6-diphenylpyrazine 1-oxide 
• 1489-06-1 2,3-diphenyl-5,6-dihydropyrazine 

Downstream Products

• 104369-41-7 3,5,6-triphenylpyrazin-2-(1H)-one 
• 17705-32-7 5,6-diphenyl-1H-pyrazine-2-thione 
• 41270-66-0 2-chloro-5,6-diphenylpyrazine 
• 243472-70-0 2-bromo-5,6-diphenylpyrazine 
• 25468-60-4 3-bromo-5,6-diphenyl-1H-pyrazin-2-one 
• 25468-58-0 3-nitro-5,6-diphenyl-1H-pyrazin-2-one 
• 62251-28-9 1-methyl-5,6-diphenylpyrazine-2(1H)-one 
• 34121-90-9 5-Methoxy-2,3-diphenyl-1,4-diazabenzene 
• 475084-96-9 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butyl ester 
• 475086-75-0 4-[N-(5,6-diphenylpyrazine-2-yl)-N-isopropylamino]-1-butanol 
• 475085-57-5 MRE-269 
• 475086-01-2 Selexipag 

Relevant articles and documents

Discrimination in the solid-state photodimerization of 1-methyl-5,6- diphenylpyrazin-2-one

1-Methyl- and 1-ethyl-5,6-diphenylpyrazin-2-one crystallize in two modifications, one of which is light-stable and the other light-sensitive. The light-sensitive modification is known to undergo photodimerization in the solid state. This polymorph crystallizes in the monoclinic space group P21 with two crystallographically independent molecules in the asymmetric unit. The molecules are packed in stacks running parallel to the unique b axis. The two independent molecules are arranged alternately along the stack. In principle, there are two different pairs of molecules within a stack that can undergo photodimerization, and each should form a different enantiomer. A large crystal was irradiated and a solution of the product was separated by HPLC. The optical purity of the (+)-enantiomer sample was estimated to be greater than 90%. This finding indicates that only one of the two pairs undergoes photoreaction. The structure of a single crystal of the pyrazinone was elucidated by X-ray diffractometry before and after irradiation with a laser at a wavelength of 488 nm to 19% conversion. The results of the crystal-structure determinations provide additional evidence that only one of the two pairs of molecules undergoes photodimerization although there are no significant differences between the distances between the reacting centers. Furthermore, the latter results suggest that weak hydrogen bonds are a dominant factor that determines which of the two pairs is dimerized upon irradiation. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Synthesis method of diphenyl pyrazine derivative

The invention discloses a synthesis method of a diphenyl pyrazine derivative. The method is characterized in that benzil and glycinamide are used as raw materials, and a target product is prepared through five-step reaction. The obtained target product is high in purity, subsequent production of high-quality drugs is facilitated, and the synthesis method is reasonable in route design, mild in reaction condition, free of high-temperature reaction, good in safety and high in feasibility.

AN IMRPOVED PROCESS FOR THE PREPARATION OF SELEXIPAG OR ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention provides an improved process for Selexipag of formula (I) or its pharmaceutically acceptable salts.