Month: August 2021

Application of 4858-85-9, 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. 4858-85-9, name is 2,3-Dichloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

2,3-Dichloropyrazine (5.00 g, 33.56 mmol, 1.00 eq) was mixed with ammonia (68.27 g, 1.95 mol, 58.04 eq). The mixture was stirred at 85 C for 12 hours, concentrated under reduced pressure. The residue was purified by silica gel chromatography (column height: 250 mm, diameter: 100 mm, 100 to 200 mesh silica gel, petroleum ether / ethyl acetate = 50/1, 20/1) to deliver 3-chloropyrazine-2-amine (700.00 mg, 5.40 mmol, 16.09% yield) as a white 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, 2,3-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Medshine Discovery Inc.; LUO, Wei; DING, Charles Z.; HUANG, Zhigang; CHEN, Shuhui; (162 pag.)EP3252059; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, 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 23611-75-8, category: Pyrazines

Methyl 6-(chloropyrazine)-2-carboxylate (13) (2g, 0.0115mmol) was dissolved in 80mL of 87 DMSO. 88 Sodium azide (3g, 0.0463mmol) and 39 triphenylphosphene (4.6g, 0.1738mmol) were added and refluxed at 120C for 4h. 20mL of 1N 89 HCl was added and the reaction was continued at 120C for 2h. The mixture was cooled and neutralized by aqueous NaHCO3 solution and 131 product was extracted in ethyl acetate, dried with Na2SO4 which was then concentrated and dried with n-pentane to get 1.4g of compound 14 as yellow solid (yield 82.4%). 1H NMR (400MHz, DMSO-d6) delta 8.28-8.27 (m, 1H), 8.07 (s, 1H), 6.90 (s, 2H), 3.84 (s, 3H). C6H7N3O2 [M]: 153.14; MS (ESI) m/z: [M+H]+: 154.05

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, Methyl 6-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Trivedi, Prakruti; Adhikari, Nilanjan; Amin, Sk. Abdul; Jha, Tarun; Ghosh, Balaram; European Journal of Pharmaceutical Sciences; vol. 124; (2018); p. 165 – 181;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 17231-51-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 17231-51-5 name is 3-Amino-6-bromopyrazine-2-carbonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate H (0192) 3-Amino-6-(4-chloro-2-fluorophenyl)pyrazine-2-carbonitrile (0193) To a solution of 3-amino-6-bromopyrazine-2-carbonitrile (2.00 g, 9.55 mmol) in 1,4-dioxane (48 mL), were added (4-chloro-2-fluorophenyl)boronic acid (1.66 g, 9.55 mmol) and aqueous Na2CO3 (2 M, 24 mL, 48 mmol) and the reaction mixture sparged with N2 gas for 10 min. Pd(dppf)Cl2.CH2Cl2 (0.349 g, 0.477 mmol) was then added and the reaction mixture sparged for an additional 10 min with N2 gas. The reaction vessel was sealed and heated for 3 hours at 80 Celsius. The mixture was cooled to rt, filtered through celite, and the filter cake washed with EtOAc (300 mL). The filtrate was washed with a 1:1 mixture of brine/H2O (2×100 mL). The organic phase was concentrated to dryness and subjected to FCC to give the title compound (1.99 g, 84%). MS (ESI): mass calcd. for C11H6ClFN4, 248.03; m/z found 249.0 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.67 (d, J=2.0, 1H), 7.83 (m, 1H), 7.25-7.08 (m, 2H), 5.36 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Amino-6-bromopyrazine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Bacani, Genesis M.; Eccles, Wendy; Fitzgerald, Anne E.; Goldberg, Steven D.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Lee-Dutra, Alice; Liu, Jing; McClure, Kelly J.; Meduna, Steven P.; Pippel, Daniel J.; Rosen, Mark D.; Sales, Zachary S.; US2015/259357; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 89283-32-9 as follows. Recommanded Product: 89283-32-9

[0291] To a mixture of(3-chloropyrazin-2-yl)methanol (200 mg, 1.4 mmol, 1 eq.), 1- isopropyl-5-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)-1H-pyrazole (393 mg, 1.67 mmol, 1.2eq.), Pd(dppf)C12 (102 mg, 0.14 mmol, 0.1 eq.), and K2C03 (580 mg, 4.2 mmol, 3 eq.) in aRB flask were added dioxane (6 mL) and water (2 mL). The mixture was heated at 100 C for 1 h, cooled to rt, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-( 1 -isopropyl- 1 H-pyrazol-5-yl)pyrazin-2-yl)methanol (110 mg, 36%) as a yellow oil. LRMS(M+H+ ] m/z 219.1.

According to the analysis of related databases, 89283-32-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley; WO2013/102145; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 14508-49-7, A common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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.

Intermediate 741 ,1 -Dimethylethyl (2-{4-r(2S,4/?)-1 -acetyl-2-methyl-4-(2-pyrazinylamino)-1 , 2,3,4- tetrahvdro-6-quinolinyll-1 /-/-pyrazol-1 -yl)ethyl)methylcarbamateA flask was charged with 2-chloropyrazine (138 mg, 1 .209 mmol) and treated at room temperature under nitrogen with a solution of 1 ,1-dimethylethyl [2-(4-{(2S,4/?)-1 -acetyl-2- methyl-4-amino-1 ,2,3,4-tetrahydro-6-quinolinyl}-1 H-pyrazol-1 -yl)ethyl]methylcarbamate (for a preparation see intermediate 55) (250 mg, 0.605 mmol) in 1 ,4-dioxane (5 mL). 2′- (dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (DavePhos) (47.6 mg, 0.121 mmol), sodium tert-butoxide (1 16 mg, 1 .209 mmol) and tris(dibenzylideneacetone)dipalladium(0) (55.4 mg, 0.060 mmol) were added and the resulting mixture was stirred under nitrogen at 1 10C for 16 h then cooled to room temperature and partitioned between EtOAc (25 mL) and water (25 mL). The layers were separated and the aqueous phase was extracted with EtOAc (25 mL). The combined organic phases were washed with brine (50 mL), dried over Na2S04 and concentrated in vacuo. Purification of this residue on SP4 using a 25 G silica cartridge (gradient: 1 to 5% MeOH in DCM) gave 1 ,1 -dimethylethyl (2-{4-[(2S,4R)-1 -acetyl-2-methyl-4-(2- pyrazinylamino)-1 ,2,3,4-tetrahydro-6-quinolinyl]-1 H-pyrazol-1 -yl}ethyl)methylcarbamate (204.6 mg, 0.344 mmol, 56.9 % yield) as an orange oil.LCMS (Method B): Retention time 0.89 min, [M+H]+ = 506.23

The synthetic route of 14508-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GOSMINI, Romain, Luc, Marie; WO2011/54848; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 486460-21-3,Some common heterocyclic compound, 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, molecular formula is C6H7F3N4, 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.

Bis (trichloromethyl) carbonate (BTC) (495 mg, 1.7 mmol) was dissolved in 10 ml of methylene chloride and cooled in an ice-salt bath to reduce the internal temperature to -5 C to 0 C. (1.013 g, 4.2 mmo 1) was added to a mixture of pyridine (725 mg, 9.2 mmol) and 1- (2,3-difluoro-6-nitrophenyl) piperazine at 0 C, Omin added, maintained at 0 C reaction lh, directly to the next reaction.To the above reaction solution was added 3- (trifluoromethyl) -5,6,7,8-tetrahydro- [1,2,4] triazolo [4,3-a] pyrazine (800 mg, And triethylamine (842 mg, 8.4 mmol). The temperature of the reaction system was raised to room temperature and stirred for 20 h. The reaction was quenched by the addition of 20 ml of saturated sodium bicarbonate solution and extracted with dichloromethane (20 ml of X2). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated and purified by column chromatography (petroleum ether: ethyl acetate = 3: 2) Yellow solid, 1.254 g, 48.1% yield in three steps.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, its application will become more common.

Reference:
Patent; Shanghai Institute Of Pharmaceutical Industry; China State Institute of Pharmaceutical Industry; Meng, Xiangguo; Cai, Zhengyan; Zhou, Weicheng; Jiang, Jingzhang; Zhu, Yijun; Ge, Yuanyuan; Yan, Pingping; (32 pag.)CN103172635; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 193966-70-0, 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. 193966-70-0, name is Methyl 5-(bromomethyl)pyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A solution of methyl 5-(bromomethyl)pyrazine-2-carboxylate (0.567 g, 2.453 mmol) and potassium iodide (0.039 g, 0.234 mmol) in N,N-dimethylformide (6 mL) was stilTed at the room temperature for 30 mm, and mixed with Nphenylmethanesulfonamide (0.400 g, 2.336 mmol) and potassium carbonate (0.420 g, 3.037 mmol). The reaction mixture was stirred at the same temperature for additional 8 hr. The reaction mixture was diluted with water and stirred. The resulting precipitates were collected by filtration, washed by water, and dried to give methyl 5-((N-phenylmethylsulfonamido)methyl)pyrazine-2-carboxylate as white solid (0.710 g, 94.6 %).

The chemical industry reduces the impact on the environment during synthesis Methyl 5-(bromomethyl)pyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 54608-52-5, name is 2-Hydrazinopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C4H6N4

General procedure: A mixture of amidrazone 1a (1.00 g, 0.0047 mol), benzaldehyde (2a)(0.50 g, 0.0047 mol), PEG-300 (5 mL) and CAN (5 mol%) was heated at 80 C for 1 h (Table 2). After completion of the reaction as monitored by TLC, the mixture was cooled to r.t. and extracted with Et2O (3 × 20mL). The combined organic layers were washed with H2O (2 × 30 mL) and aq NaHCO3 solution (2 × 30 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (EtOAc-hexane, 1:1) to afford pure 3a.

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nakka, Mangarao; Tadikonda, Ramu; Rayavarapu, Srinuvasarao; Sarakula, Prasanthi; Vidavalur, Siddaiah; Synthesis; vol. 47; 4; (2015); p. 517 – 525;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-28-4, A common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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.

Step-1: Synthesis of 6-chloro-5-iodopyrazin-2-amine To a stirred solution of 2-amino-6-chloropyrazine (2.0 g, 1.0 eq., 15.50 mmol) in acetonitrile (20 mL) was added NIS (3.46 g, 1.0 eq., 15.50 mmol) at 0 C. The reaction was allowed to stir at RT. Progress of the reaction was monitored by TLC and LCMS After completion of the reaction the solvent was evaporated under vacuum and the solid was extracted using ethyl acetate (3*100 mL). The combined organic layers were washed (brine), dried (anhydrous Na2SO4) and concentrated under vacuum to get the solid which was purified by normal phase column chromatography to get the desired product (1.7 g, 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:
Patent; GiraFpharma LLC; PHAM, Son Minh; CHEN, Jiyun; ANSARI, Amantullah; JADHAVAR, Pradeep S.; PATIL, Varshavekumar S.; KHAN, Farha; RAMACHANDRAN, Sreekanth A.; AGARWAL, Anil Kumar; CHAKRAVARTY, Sarvajit; (120 pag.)US2019/23666; (2019); 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. 5049-61-6, name is Pyrazin-2-amine, A new synthetic method of this compound is introduced below., category: Pyrazines

2-Aminopyrazine (100 mg, 1.1 mmol) and bromoacetaldehyde dimethylacetal (253 mg, 1.6 mmol) were dissolved in ethanol (4.5 ml), hydrobromic acid (48%, 0.5 ml) added and the mixture was heated under reflux for 18 h. The solution was allowed to cool to room temperature then pre-adsorbed directly onto silica. Purification by silica gel chromatography eluding with dichloromethane and 1% conc. ammonia on a gradient of methanol (1-4%) gave imidazo[1,2-alpha]pyrazine (90 mg, 72%) as a white crystalline solid: deltaH (360 MHz, CDCl3) 6.70 (1H, s), 7.82 (1H, s), 7.88 (1H, d, J 4), 8.29 (1H, d, J 4), 9.12 (1H, s).

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; Goodacre, Simon Charles; Hallett, David James; Street, Leslie Joseph; US2004/19057; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem