Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 4774-14-5, name is 2,6-Dichloropyrazine, belongs to Pyrazines compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4774-14-5, name: 2,6-Dichloropyrazine

General procedure: To a solution of absolute ethanol (5 mL) and dichlorodiazine (3.36 mmol) in a 50mL round-bottom flaskwas added triethylamine (5.03 mmol), followed by the amine (5.03 mmol). The mixture was stirred either under reflux of ethanol (for dichloropyridazine and for dichloropyrazine) or at room temperature (for dichloropyrimidines). The reaction was monitored by GC. Once the starting dichlorodiazinewas completely consumed, the mixture was poured into a saturated NH4Cl solution (20 mL), then extracted with CH2Cl2 (320 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated under vacuum. The crude solid was triturated in petroleum ether, filtered through a Buchner to afford the pure product.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Sengmany, Stephane; Lebre, Julie; Le Gall, Ewan; Leonel, Eric; Tetrahedron; vol. 71; 29; (2015); p. 4859 – 4867;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C5H2ClN3

The starting compound 3-chloropyrazine-2-carboxamide was synthesized using two published procedures. The first method was classified as less effective and was based on the homolytic amidation of 2-chloropyrazine. Thus, 2-chloropyrazine (0.17 mol) was dissolved in formamide (3.7 mol), heated to 90 C and ammonium peroxodisulphate (0.18 mol) was added portionwise over one hour period. This mixture reacted for another one hour at 90 C and then it was left to stand for 24 h at laboratory temperature. Dilution with 100 mL of water was followed by filtration and this filtrate was extracted continuously with chloroform for 16 h [34,42]. The mixture of three positional isomers was separated by flash chromatography using silica gel as stationary phase. The second process used 3-chloropyrazine-2-carbonitrile, which was submitted to partial hydrolysis of the nitrile group. The powdered carbonitrile (0.104 mol) was added little by little into the reaction mixture of concentrated hydrogen peroxide (0.95 mol) and water (195 mL) heated to 50 C. The pH was adjusted and regulated around a value of 9 using an 8% solution of sodium hydroxide and the temperature of the reaction was regulated between 55 and 60 C. The reaction was stopped after 2.5 h and was cooled to 5 C. Newly-emerged crystals were removed by suction and recrystallized from ethanol [42].

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Jandourek, Ondrej; Dolezal, Martin; Kunes, Jiri; Kubicek, Vladimir; Paterova, Pavla; Pesko, Matus; Buchta, Vladimir; Kralova, Katarina; Zitko, Jan; Molecules; vol. 19; 7; (2014); p. 9318 – 9338;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 123-32-0, name is 2,5-Dimethylpyrazine, belongs to Pyrazines compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 123-32-0, Application In Synthesis of 2,5-Dimethylpyrazine

(b) 3,6-Dimethylpyrazin-2-amine A mixture of 2,5-dimethylpyrazine (14 g, 0.13 mol) in N,N-dimethylaniline (50 mL) was heated to 170 C. and NaNH2 (22 g, 0.56 mol) was added in portions. The reaction mixture was stirred at 170 C. for 1 h, and the solvent was removed. The product was purified by silica gel column chromatography to give 3,6-dimethylpyrazin-2-amine as a brown solid (1.6 g, yield 10%). ESI MS: m/z 124 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,5-Dimethylpyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Sunovion Pharmaceuticals Inc.; US2012/178748; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 4774-14-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4774-14-5, name is 2,6-Dichloropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2,6-dichloropyrazine (2.5 g, 16.8 mmol, 1.0 equiv),/?- ? toluenesulfonic acid (6.4 g, 33.6 mmol, 2.0 equiv), sodium iodide (20.0 g, 133.3 mmol, 8.0 equiv), 15-crown-5 (2.0 mL) and sulfolane (40 mL) was heated at 150 0C and stirred in a sealed tube for 2 hr. After cooling, water (100 mL) was added to the reaction mixture. The mixture was then neutralized with a saturated solution of sodium hydrogencarbonate, and washed with a saturated solution of sodium thiosulfate. The mixture was extracted with diethyl ether (5 x 100 mL). The ether extracts were dried (Na2SO4) and concentrated in vacuo. 2,6-Diiodopyrazine was precipitated with 10 mL of water, filtered, washed with water and pentane to provide a pale yellow powder after lyophilization (2.1 g, 38%). 1H NMR (400 MHz, CDCl3) delta 8.74 (s, 2H); MS (M+H)+ = 332, R1= 1.29 min.

The synthetic route of 2,6-Dichloropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; XENON PHARMACEUTICALS INC; WO2008/24390; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 6164-79-0, name is Methyl 2-pyrazinecarboxylate, molecular formula is C6H6N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. COA of Formula: C6H6N2O2

Pyrazine-2-carboxylic acid hydrazide. To a stirred solution of pyrazine-2-carboxylic acid methyl ester (11.1 g, 80 mmol) in 140 mL OF ETOH was added hydrazine hydrate (15.6 ML, 320 mmol). The resultant solution was heated to reflux for 2h. The solvent was removed under reduced pressure and dried under high vacuum to yield the title amide (11.1 g, 100%) as a white solid. The product was used in subsequent steps without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6164-79-0, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/16909; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 6-chloropyrazine-2-carboxylate

A mixture of l-(4-((4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)methyl)benzyl)pyridin-2(lH)-one (339 mg, 1.05 mmol, 3.0 eq), methyl 6-chloropyrazine-2-carboxylate (150 mg, 0.87 mmol, 1.0 eq), Pd(dppf)Ci2 (71 mg, 0.061 mmol, 0.1 eq), K2C03 (240 mg, 1.74 mmol, 2.0 eq) in toluene/dioxane/H20 (10 niL/1 niL/1 mL) under N2 was stirred at 100 C for 5 h and then concentrated. The residue was extracted with EA (50 mL X 3). The combined organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was purified via pre-TLC to afford methyl 6-(4-((2-oxopyridin-l(2H)-yl)methyl)benzyl)pyrazine-2-carboxylate as a white solid (100 mg, 34%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 23611-75-8.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 95-89-6,Some common heterocyclic compound, 95-89-6, name is 3-Chloro-2,5-dimethylpyrazine, molecular formula is C6H7ClN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Ammonia in water (3 mL, 48.5 mmol) was added to 3-chloro-2,5-dimethylpyrazine (0.121 mL, 1 mmol) and the mixture heated by microwaves to 165 C. for 7 hours. Following LCMS analysis, the reaction was then reheated to 165 C. for a further 16 hours, by microwaves. After cooling, the solvent was removed under a stream of nitrogen and the crude redissolved in dichloromethane (20 mL). Water (25 mL) was added and the mixture basified to pH14 using sodium hydroxide solution (18 N). The organic layer was removed and the aqueous layer extracted with dichloromethane (5¡Á25 mL). The organic phases were combined and dried using a hydrophobic frit, then evaporated in vacuo to give the title product (109 mg). This was used directly in the next step with no further purification. LCMS (2 min, high pH) Rt 0.47 min, m/z (ES+) 124 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 7.73 (s, 1H), 4.42 (br. s., 2H), 2.37 (s, 3H), 2.35 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-2,5-dimethylpyrazine, its application will become more common.

Reference:
Patent; Glaxo Group Limited; Birault, Veronique; Campbell, Amanda Jennifer; Harrison, Stephen; Le, Joelle; Shukla, Lena; US2015/65507; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 4744-50-7,Some common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, molecular formula is C6H2N2O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

5.1.26 13-[(Methyloxy)carbonyl]-2-pyrazinecarboxylic acid (35) 16 2,3-Pyrazinedicarboxylic anhydride (34) (15.3 g, 102 mmol) was dissolved in methanol (100 mL) and the solution was stood at room temperature for 3 days. The solvent was removed under reduced pressure and the residue was crystallised from ethyl acetate to give 35 (13.85 g, 75%): MS ES+ve m/z 183 (M+H)+; 1H NMR delta (DMSO-d6) 8.91 (1H, d, J 2 Hz), 8.90 (1H, d, J 2 Hz), 3.90 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Pyrazinecarboxylic anhydride, its application will become more common.

Reference:
Article; Procopiou, Panayiotis A.; Browning, Christopher; Gore, Paul M.; Lynn, Sean M.; Richards, Stephen A.; Slack, Robert J.; Sollis, Steven L.; Bioorganic and Medicinal Chemistry; vol. 20; 20; (2012); p. 6097 – 6108;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 486460-21-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

DIPEA (0.307 mL, 1.759 mmol) was added to a mixture of 3-(trifluoromethyl)-5,6,7,8- tetrahydro-[ 1 ,2,4jtriazolo[4,3-ajpyrazine (127 mg, 0.660 mmol), cis-1 -(6-chloro-3- cyanoquinolin-4-yl)-2-methylpiperidine-4-carboxylic acid (145 mg, 0.440 mmol), and HATU(334 mg, 0.879 mmol) in DMF (4 mL) and stirred at 18 C for 3 h. The reaction was quenchedwith water (30 mL) and extracted with EtOAc (30 mL x 4), the combined organic phases were washed with brine (30 mL), dried over Na2SO4, filtered. The filtrates were concentrated and purified by p-HPLC to give cis-6-chloro-4-(2-methyl-4-(3-(trifluoromethyl)-5 ,6,7, 8-tetrahydro- [1 ,2,4jtriazolo [4,3-ajpyrazine-7-carbonyl)piperidin- 1 -yl)quinoline-3 -carbonitrile. MS: 504 (M + 1). The product was resolved by SFC (Column: Chiralpak AD-3 Mobile phase: A: CO2 B: methanol (0.05% DEA) Gradient: from 5% to 40% of B SFC separation gave peak 1(70mg, 0.135 mmol) MS: 504 (M + 1); and peak 2 (R,R or S,S) MS: 504 (M +1)

The synthetic route of 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CUMMING, Jared, N.; DYKSTRA, Kevin, D.; HRUZA, Alan; LI, Derun; LIU, Hong; TANG, Haiqun; TAOKA, Brandon, M.; VERRAS, Andreas; WALSH, Shawn, P.; WU, Wen-Lian; (170 pag.)WO2018/34918; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 63286-28-2

Step 1 : To a solution of tetrahydrofuran-3-carboxylic acid (1 .0 g, 8.6 mmol) in DMF (15 ml) was added HATU (3.60 g, 9.47 mmol), DIPEA (1 .22 g, 1 .66 ml, 9.47 mmol) and finally 2-chloro-3-hydrazinylpyrazine (1 .37 g, 9.47 mmol). The mixture was stirred for 3 hours at RT. The reaction mixture was poured into sat. aq. Na2CO3 (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic phases were washed with brine (3×25 mL), dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography using a gradient of ethyl acetate and heptane to yield 1 .1 g (53%) A/’-(3-chloropyrazin-2-yl)tetrahydrofuran-3- carbohydrazide.

According to the analysis of related databases, 63286-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; JESSING, Mikkel; (126 pag.)WO2016/55618; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem