Month: August 2021

Application of 36070-79-8, 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. 36070-79-8, name is 6-Chloropyrazine-2-carboxamide belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 150 mg (0.952 mmol) of 5-Cl-PZA (1) or 6-Cl-PZA (2) was dissolved in ethanol together with triethylamine (1 eq., 96 mg, 0.952 mmol). Three equivalents of corresponding alkylamine were added to the reaction mixture and refluxed in ethanol generally for 6 hours. The completion of the reaction was checked by TLC chromatography (eluent: hexane/ethyl acetate, 1:2). The crude product was absorbed on silica by solvent evaporation and purified by flash chromatography (hexane/ethyl acetate gradient elution).

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

Reference:
Article; Servusova, Barbora; Paterova, Pavla; Mandikova, Jana; Kubicek, Vladimir; Kucera, Radim; Kunes, Jiri; Dolezal, Martin; Zitko, Jan; Bioorganic and Medicinal Chemistry Letters; vol. 24; 2; (2014); p. 450 – 453;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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 939412-86-9, name: (3-Chloropyrazin-2-yl)methanamine hydrochloride

Into a round bottom 1-neck flask (5L), 3-oxo-cyclobutanecarboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester (217.2 g, 0.937 mol), C-(3-chloro-pyrazin-2-yl)-methylamine hydrochloride salt (153.3 g, 0.852 mol), and THF (760 mL) were added. A solution of 10% NaHCO3 (1.07 kg) was then added and after 20 min, the layers were allowed to separate and the aqueous layer was removed. The aqueous layer was back extracted with EtOAc (1×700 mL, 1×300 mL). The combined organics were washed with brine (350 mL), dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound. This solid was resuspended in ethyl acetate (915 mL) and DMF (132 mL) and the solution was put under an atmosphere of nitrogen and cooled to 10.5 C. Phosphorus oxychloride (159 mL, 1.70 mol) was then added over 15 minutes and the reaction was allowed to stir for 45 min. The reaction solution was then poured slowly into a 22% aqueous Na2CO3 solution at 10IC. Water (1 L) was added and the layers were allowed to separate. The organic layer was removed and the aqueous was back extracted with EtOAc (1×1 L, 1×0.5 L). The combined organic phases were dried over MgSO4, filtered, and concentrated in vacuo until about 0.5 L of solvent remained. Heptane was added and the slurry was concentrated in vacuo until most of the EtOAc was removed. The resultant slurry was filtered to give desired product. 1H NMR (400 MHz, CDCl3) delta 3.59-3.68 (m, 2H), 3.72-3.79 (m, 2H), 3.86-3.94 (m, 1H), 7.40 (d, 1H, J=5.2 Hz), 7.60 (d, 1H, J=5.2 Hz) and 7.85 (s, 1H).

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:
Patent; Buck, Elizabeth A.; Griffin, Graeme; Barr, Sharon M.; US2007/280928; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 143591-61-1,Some common heterocyclic compound, 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, molecular formula is C6H3BrClN3, 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.

Add 3-bromo-8-chloroimidazo [1,2-a] pyrazine (1.33 g, 5.7 mmol), 1-methyl-1H-pyrazole-4-amine (0.66 g, 6.8 mmol)And triethylamine (1.15 g, 11.4 mmol) were added to 15 mL of n-butanol, and the temperature was raised to 120 C. and reacted overnight.The solvent was removed by rotary evaporation, diluted with 30 mL of water, and extracted with ethyl acetate (20 mL * 3). The organic phases were combined,It was washed with 20 mL of saturated brine, dried over anhydrous sodium sulfate, and concentrated.1.25 g of a pale yellow solid was isolated on a silica gel column with a yield of 75%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, its application will become more common.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Xing Qingfeng; Ai Yixin; (85 pag.)CN110272426; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 38557-72-1, 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. 38557-72-1, name is 2-Chloro-3,5-dimethylpyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step 4: Synthesis of 3,5-Dimethyl-2-(7-phenylnaphthalen-2-yl)pyrazine (abbreviation: Hdm7p2npr)First, into a recovery flask equipped with a reflux pipe were placed 0.62 g of 2-chloro-3,5-dimethylpyrazine, 1.07 g of 7-phenylnaphthalene-2-boronic acid, 0.46 g of sodium carbonate, 0.020 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2), 10 mL of water, and 10 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was irradiated with microwaves (2.45 GHz, 100 W) for 15 minutes, so that heating was performed. Then, the reaction container was cooled to 50 C. or less. Water was added to the reaction solution, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled, and the obtained residue was purified by silica gel column chromatography with a developing solvent of dichloromethane, whereby Hdm7p2npr, which is the pyrazine derivative to be produced, was found to be obtained (as a white powder in 65% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 4 is illustrated in the following (d-5).

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-Chloro-3,5-dimethylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US2011/245495; (2011); 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. 290-37-9, name is Pyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C4H4N2

A 250 ml round bottom flask was first placed in an ice-water bath followed by the addition of 0.01 mmol of pyrazine,0.05 mol acetaldehyde (dissolved in 15 ml of water), 15 ml of glacial acetic acid and 3 ml of concentrated sulfuric acid, stirring to completely dissolve pyrazine,And then continue to stir for 10 min, slowly dropping 0.02mmol of t-butyl hydroperoxide solution, after dripping and then continue to stir for 20 min, and finally slowly dropping the concentration of 0.02mol / L ferrous sulfate solution 1ml,After the completion of the dropwise stirring for 2 h, the mixture was filtered and washed with a large amount of water to obtain 2,5-dicarboxylic acid pyrazine.

The synthetic route of 290-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University of Light Industry; LI, XILI; ZHOU, LIMING; LI, CAIFENG; GAO, LIJUN; FANG, SHAOMING; (15 pag.)CN103896972; (2016); B;,
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. 41110-33-2, name is Methyl 5-methylpyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 41110-33-2

A solution of lithium aluminum hydride (164.0 mL, 0.164 mol, 1.0 M in THF, 0.5 equiv.) was added to a suspension of methyl 5-methylpyrazine-2-carboxylate (50 g, 0.328 mol, 1.0 equiv.) in anhydrous THF (750 mL) at -78 C. The internal temperature was kept below -72 C during the addition of lithium aluminum hydride. On completion of addition, the reaction mixture was stirred at -78 C for a further 20 min and then quenched with glacial AcOH (50.0 mL) at the same temperature. The resulting mixture was warmed to RT and the volatiles were removed by evaporation under vacuum. The residue was dissolved in hydrochloric acid (1.5 N, 500 mL) and extracted with DCM (2 x 2 L). The combined organic layers were washed with a saturated aqueous sodium hydrogen carbonate solution (2 x 500 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to yield a brown oil. The intial product was purified by column chromatography (silica gel 60-120 mesh) eluting with a gradient of 10% EtOAc in petroleum ether to provide the title compound as a pale yellow liquid (21.3 g, 53 %). TLC Info: (9.0/1.0 Petroleum ether/EtOAc). 1H NMR (400 MHz, CDCl3) delta 10.14 (s, 1H), 9.07 (d, J = 1.5 Hz, 1H), 8.63 (d, J = 1.4 Hz, 1H), and 2.70 (s, 3H). LCMS-ESI (pos.) m/z: 123 (M+H)+.

According to the analysis of related databases, 41110-33-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; CHENG, Alan C.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; PATTAROPONG, Vatee; SWAMINATH, Gayathri; KREIMAN, Charles; MOEBIUS, David C.; SHARMA, Ankit; (543 pag.)WO2018/93580; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, 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. Recommanded Product: 2-Amino-5-bromopyrazine

5- Bromo-pyrazin-2-ylamine was combined with copper (I) iodide (1.3 g, 6.9 mmol) , potassium cyanide (0.44 g, 6.8 mmol), tetrakis (triphenylphosphine) palladium (0) (0.95 g, 0.83 mmol), and 18-crown-6 (0.058 g, 0.22 mmol) in DMF (15 mL) . The resulting mixture was stirred for 40 min, then heated at reflux (155C) for 2 h. The reaction was cooled to room temperature, then allowed to stand overnight. The precipitate was separated by filtration and the filtrate was concentrated to dryness in vacuo. The orange-colored residue was taken up in EtOAc and hexanes and an initial precipitate was formed, then separated by filtration. Upon standing, additional precipitate formed in the mother liquor and was collected by filtration. The solids were combined to yield 0.10 g of a bright orange solid.

The synthetic route of 2-Amino-5-bromopyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICOS CORPORATION; WO2006/105262; (2006); 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. 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Methyl 3,5-dichloropyrazine-2-carboxylate

The mixture of methyl 3,5-dichloropyrazine-2-carboxylate (1.0 g, 4.83 mmol), (3L’)- l,3-dihydrospiro[indene-2,4′-piperidin]-3-amine dihydrochloride (1.65 g, 4.83 mmol, Intermediate I) and CsF (3.66 g, 24.1 mmol) in DMF (15 mL) was stirred at 70 C for 2 hours. BOC20 (1.57 g, 7.24 mmol) and TEA (1 mL) were added to the mixture and the mixture was stirred at 20 C for 1 hour. The mixture was diluted with H20 (50 mL), extracted with EtOAc (50 mL x 2). The organic layer was washed with brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure and the residue was purified by column chromatography (petroleum ether / ethyl acetate = 1 : 0 ~ 5 : 1) to afford methyl 5-[(3ri)-3-{[(/er/-butoxy)carbonyl]amino}-l,3-dihydrospiro[indene-2,4′-piperidin]-r- yl]-3-chloropyrazine-2-carboxylate (1.58 g, 69% yield) as a yellow solid and methyl 3-[(3L’)- 3-{[(/er/-butoxy)carbonyl]amino}-l,3-dihydrospiro[indene-2,4′-piperidin]-l’-yl]-5- chloropyrazine-2-carboxylate (320 mg, 14% yield) as a yellow solid. LCMS m/z (M+H)+ = 473.1 for both isomers.

The synthetic route of 330786-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 875781-43-4, 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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Bromo-7-fluoro-5H-pyrrolo [2,3-b] pyrazine preparation 2-Bromo-5H-pyrrolo [2,3-b] pyrrole (500 mg, 2.52 mmol), 1-chloromethyl-4-fluoro -1,4-monocyclo-bicyclo [2.2.2.] Octane difluoroborate (3616 (^? 1111? ‘893 11 ^, 2.52 (2 mL) and acetonitrile (6 mL). The mixture was stirred at room temperature for 2 h and then heated to 80 (TC for 48 h, then cooled to room temperature, concentrated, Purification by column & ‘ gave the title compound as an off-white solid which was used directly in the next step.

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-Bromo-5H-pyrrolo[2,3-b]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NANJING SHENGHE PHARMACEUTICAL CO., LTD.; WANG, YONG; ZHAO, LIWEN; LIU, YANG; ZHANG, JINGZHONG; WANG, DEZHONG; GAO, YIPING; CHEN, HONGYAN; ZHANG, CANG; ZHANG, DI; (68 pag.)TWI523856; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 762240-92-6, 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. 762240-92-6 name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, 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.

General procedure: A solution of 3-(trifluoromethyl)-5,6,7,8-tetrahydro [1,2,4]triazolo[4,3-a]pyrazine hydrochloride salt 9 (1.0 eq.) in dimethylformamide (DMF, 2e3 mL) was added potassium carbonate (2.5eq.) at 5 C and stirred for 15 min at room temperature. To this,various chloride derivatives (1.0 eq.) in DMF was added to reaction mixture at same temperature. The resultant reaction mixture was allowed to stir at room temperature for 24 h. The completion of the reaction was monitored on TLC (using 10% MeOH: DCM and ammonia as a modifier as mobile phase). The reaction mixture was poured into ice-cold water and extracted with ethyl acetate(2 x 15 mL). Organic layers were combined and the combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford crude material and crystallized it from methanol to get 3-(trifluoromethyl)-5,6,7,8-tetrahydro [1,2,4]triazolo [4,3-a]pyrazine derivatives (12f-12j) in good practical yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Jethava, Divya J.; Acharya, Prachi T.; Vasava, Mahesh S.; Bhoi, Manoj N.; Bhavsar, Zeel A.; Rathwa, Sanjay K.; Rajani, Dhanji P.; Patel, Hitesh D.; Journal of Molecular Structure; vol. 1184; (2019); p. 168 – 192;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem