Month: February 2021

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: 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

Reference of 19745-07-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 19745-07-4 as follows.

Step F: (S)-3 -(2-fluoro-4-(5-methyl- 1 ,3 ,4-oxadiazol-2-yl)phenoxy)- 1 -(piperidin-4-yl)pyrrolidin-2-one 2,2,2-trifluoroacetate (150 mg, 0.316 mmol) was dissolved in DMSO (3 mL) and 2,5-dichloropyrazine (70.7 mg, 0.474 mmol) and N-ethyl-N- isopropylpropan-2-amine (138 mu, 0.790 mmol) were added and the reaction heated to 100 ¡ãC overnight. The reaction was cooled and diluted with water, extracted with EtOAc, washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified twice over silica gel (100percent EtOAc) to afford (S)-l-(l-(5-chloropyrazin-2-yl)piperidin-4-yl)-3-(2-fluoro- 4-(5-methyl-l,3,4-oxadiazol-2-yl)phenoxy)pyrrolidin-2-one (15.2 mg, 0.0321 mmol, 10.2percent yield) as a red solid. Mass spectrum (apci) m/z = 473.1 (M+H).

According to the analysis of related databases, 19745-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; AICHER, Thomas Daniel; BENCSIK, Josef Roland; BOYD, Steven Armen; CONDROSKI, Kevin Ronald; FELL, Jay Bradford; FISCHER, John P.; HINKLIN, Ronald Jay; PRATT, Scott Alan; SINGH, Ajay; TURNER, Timothy M.; WO2011/146335; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 123-32-0, The chemical industry reduces the impact on the environment during synthesis 123-32-0, name is 2,5-Dimethylpyrazine, I believe this compound will play a more active role in future production and life.

BDPEP laser dye was prepared as follows (Scheme 1); Indimethyl formamide (DMF), a mixture from 2,5-dimethylpyrazine(0.5 g) and 4-(dimethylamino) benzaldhyde (2.3 g) is dissolved.Then, this mixture is cooled to 0 C. A small amount of potassiumtri-butanolate (1.55 g) was added to this mixture while stirringuntil all the raw materials were dissolved. Distilled water changedto introduce after the reaction was completed, and the productturned into isolated with chloroform. The color of the productobtained is red solid (1.4 g, 52%). The structure of the product obtainedis characterized by IR, 1H NMR and 13C NMR [15].1H NMR (CDCl3, 600 MHz): d 3.03 (s, 12H), 6.74 (d,4H,J 8.9 Hz), 6.94 (d,2H,J 16.1 Hz), 7.49 (d, 4H, J 8.9 Hz), 7.64 (d,2H, J 16.1 Hz), 8.49 (s, 2H). 13C NMR (CDCl3, 150 MHz): d 40.3,112.2, 120.7, 127.5, 132.8, 141.7, 148.0, 150.7.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2,5-Dimethylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Abdel Gawad, Sayed A.; Abou Kana, Maram T. H.; Ebeid, El-Zeiny M.; El-Daly, Samy A.; Sakr, Mahmoud A. S.; Journal of Molecular Structure; vol. 1217; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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, Formula: C4H2Cl2N2

Step 1: 3,5-dichloropyrazine-2-carboxylic acid To a solution of LDA (2.0 M heptane/tetrahydrofuran/ethylbenzene, 11.10 mL, 22.20 mmol) in THF (75 mL) at -78 C. was added a solution of 2,6-dichloropyrazine (1.44 g, 9.67 mmol) in THF (20 mL) at room temperature over 20 min. The reaction mixture was stirred at -78 C. for 1.5 h and was then added via cannula to a 3-neck flask containing dry ice at -78 C. The reaction mixture was warmed from -78 C. to RT over 21 h and then quenched with 5 M HCl. The mixture was partitioned between brine and EtOAc. The aqueous phase was acidified to pH 3.5 with 5 M HCl. The aqueous phase was extracted with EtOAc (6*) and the combined organic extracts were washed with brine (1*), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5% to 10% MeOH in DCM) gave 3,5-dichloropyrazine-2-carboxylic acid (0.408 g, 2.11 mmol, 22% yield) as a light brown solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2,6-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); 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. 4774-14-5, name is 2,6-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H2Cl2N2

To a solution of fert-butyl azetidin-3-ylcarbamate hydrochloride (LXIII) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture was added 2,6-dichloropyrazine (LXIV) (1.428 g, 9.58 mmol) and the reaction was stirred at 95C for 3 h. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous NaaSO/t, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes?hexanes:EtOAc 1 : 1) to yield fert-butyl (l-(6-chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXV) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C12H17CIN4O2 mlz 285.1 (M+H).

According to the analysis of related databases, 4774-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (253 pag.)WO2017/23996; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4744-50-7, These common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, its 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.

General procedure: Pyrazine-2,3-dicarboxylic anhydride (1.0 g, 6.7 mmol) was dissolved in tetrahydrofuran (40 mL)in an Erlenmeyer flask and the corresponding substituted aniline (6.7 mmol, 1 equiv.) was added in one dose. The reaction mixture was stirred for 1 hour at laboratory temperature. Water (30 mL) was added into the mixture followed by the saturated aqueous solution of NaHCO3 until pH 6 to form thecorresponding 3-(phenylcarbamoyl)pyrazine-2-carboxylic acid 1-18. Obtained crystals were filtered off and washed with water. The progress of the procedure was monitored by TLC eluted with thesystem water/butanol/acetic acid 5:4:1.

Statistics shows that 2,3-Pyrazinecarboxylic anhydride is playing an increasingly important role. we look forward to future research findings about 4744-50-7.

Reference:
Article; Semelkova, Lucia; Jano?cova, Petra; Fernandes, Carlos; Bouz, Ghada; Jand?Ourek, Ond?ej; Kone?na, Klara; Paterova, Pavla; Navratilova, Lucie; Kune?, Ji?i; Dole?al, Martin; Zitko, Jan; Molecules; vol. 22; 9; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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. Computed Properties of C4H2Cl2N2

A. Preparation of the intermediate compounds a) Preparation of intermediate compound 1-1 a1 ) Preparation of (1 -benzyl-piperidin-4-yl)-(3-chloro-pyrazin-2-yl)-amine; 2,3-Dichloropyrazine (10 g, 62.12 mmol) and 1 -(benzyl)-4-piperidinamine (13.73 ml_, 67.12 mmol) were dissolved in DMF (60 ml). Then Na2CO3 (10.09 g, 1 14.10 mmol) was added. The reaction was stirred at 130 0C for 16 hours. The solid was filtered off, washed with EtOAc and the solvent was evaporated till dryness. The product was dissolved in EtOAc, washed with H2O and brine, dried with MgSO4 and evaporated under vacuum. The product was used without any further purification yielding 15 g of (1 -benzyl-piperidin-4-yl)-(3-chloro-pyrazin-2-yl)-amine (74 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4858-85-9, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2008/43775; (2008); A1;,
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. 28643-16-5, name is Methyl 3-amino-5-chloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 28643-16-5

Preparation of (S)-(2-(3-chlorobenzyl)pyrrolidin-1-yl)(3-hydroxy-5-phenylpyrazin-2-yl)methanone (9-10); Step 1: Methyl 3-amino-5-chloropyrazine 2-carboxylate 9-6 (1.48 g, 7.89 mmol), phenylboronic acid (1.06 g, 8.68 mmol) and 2M aqueous sodium carbonate (15.8 mL) were mixed with toluene (12 mL) and methanol (3 mL). Palladium tetrakis(triphenylphosphine) (0.9 g, 0.97 mmol) was added. The mixture was degassed and heated under nitrogen at 85 C. for 4 h. The reaction mixture was cooled to room temperature and filtered through a pad of Celite. The filtrate was concentrated to give a mixture with compounds 9-7 and 9-8. The mixture (0.76 g) was suspended in THF (20 mL) and CH3CN (20 mL), and treated with a solution diazomethane trimethylsilane (2.0 M in ether, 2.3 mL, 4.6 mmol). The resulting solution was stirred at room temperature for 1 h, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, gradient elution with 1% MeOH-DCM to 2% MeOH-DCM) to give the desired product 9-8.

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:
Patent; CHENG, CLIFFORD; SHIPPS, JR., GERALD W.; HUANG, XIAOHUA; HUANG, YING; SHAO, NING; RAO, ASHWIN; PALANI, ANANDAN; ORTH, PETER; VOIGT, JOHANNES H.; HERR, ROBERT J.; ROSSITER, LANA MICHELE; ZENG, QI; SUN, XIANFENG; US2012/122837; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 54608-52-5, name is 2-Hydrazinopyrazine, 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 54608-52-5, Application In Synthesis of 2-Hydrazinopyrazine

1008081 Step A: 2-(5-methyl-4-nitroso-3 -phenyl- 1 H-pyrazol- 1 -yl)pyrazine. To a solution of 2-hydrazinylpyrazine (0.485 g, 4.40 mmol) in HOAc (6 mL) was added (2- (hydroxyimino)-1-phenylbutane-1,3-dione (0.765 g, 4.00 mmol) in small portions over 2 minutes. The mixture was stirred for 5 minutes and the resulting light orange suspension was stirred at 60 C for 6 hours. EtOH (1 mL) was added and the mixture was heated at 60 C for an additional 6 hours. The resulting dark green suspension was cooled to ambient temperature and the mixture was diluted with H20 (30 mL). The green suspension was stirred for 1 hour and the solid was collected via vacuum filtration. The collected solid was washed with H20 and dried in vacuum. The solid was suspended in EtOH (25 mL) and concentrated HCI (500 jiL) was added. The mixture was heated at reflux for 20 hours, cooled to ambient temperature and diluted with chilled H20 (75 mL). The mixture was treated with 1M NaOH to pH=7 and was extracted with Et20 (3X). The combined extracts were washed with saturated NaC1 and dried over MgSO4. The dried solution was filtered through packed Celite and concentrated. The residual green-yellow solid was purified on a Si02 column using step gradient elution (25% CH2C12, 50% EtOAc/hexanes) to furnish the title compound as a turquoise solid (325 mg, 3 1%). MS (apci) mlz = 266.1 (M+H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Hydrazinopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; BLAKE, James F.; BRANDHUBER, Barbara J.; HAAS, Julia; NEWHOUSE, Brad; THOMAS, Allen A.; WINSKI, Shannon L.; WO2014/78331; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem