Pyrazines

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. 6270-63-9, name is Pyrazin-2(1H)-one, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

Example 181; (1SR,2RS)-1-methyl-cyclopropane-1,2-dicarboxylic acid 2-[(5-chloro-pyridin-2-yl)-amide]1-{[2-fluoro-4-(2-oxo-pyrazin-1-yl)-phenyl]-amide}; In analogy to example 178, step 3, (1SR,2RS)-2-(5-chloro-pyridin-2-ylcarbamoyl)-1-methyl-cyclopropanecarboxylic acid methyl ester (example 178, step 2) was reacted with 1-(4-amino-3-fluoro-phenyl)-1H-pyrazin-2-one (prepared from 2-fluoro-4-iodoaniline by reaction with 1H-pyrazin-2-one, Cu(I)I, N,N’-dimethylethylenediamine and cesium carbonate in dioxane at 120 C.) to give (I SR,2RS)-1-methyl-cyclopropane-1,2-dicarboxylic acid 2-[(5-chloro-pyridin-2-yl)-amide]1-{[2-fluoro-4-(2-oxo-pyrazin-1-yl)-phenyl]-amide} as off-white solid. MS 440.3 ([M-H]-).

According to the analysis of related databases, 6270-63-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer, Markus; Zbinden, Katrin Groebke; Haap, Wolfgang; Hilpert, Hans; Himber, Jacques; Humm, Roland; Iding, Hans; Knopp, Dietmar; Panday, Narendra; Ricklin, Fabienne; Stahl, Christoph Martin; US2006/106016; (2006); A1;,
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Application of 957344-74-0, These common heterocyclic compound, 957344-74-0, name is 5,8-Dibromoimidazo[1,2-a]pyrazine, 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.

5,8-dibromoimidazo[1,2-a]pyrazine (2.75 g, 9.90 mmol) prepared in step 1, cyclopropylamine (3.4mL, 49.50 mmol),N, N- diisopropylethylamine to (3.5 mL, 19.80 mmol) was dissolved in 1,4-dioxane (33 mL), the mixture at 100C stirred for 16 hours.Neutralized by addition of a saturated aqueous solution of sodium bicarbonate to the reaction solution and ethyl acetateExtracted with Tate.The extracted organic layer was washed with water. The organic layer was dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate: n- hexane = 1: 1) to give the title compound (530 mg, 92%)

The synthetic route of 957344-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANMI PHARM. CO., LTD.; HAM, YOUNG JIN; SON, JUNG BEOM; PARK, CHANG HEE; KANG, SEOK JONG; CHOI, JAE YUL; KIM, SEO HEE; (36 pag.)KR2015/113801; (2015); A;,
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Reference of 16298-03-6, The chemical industry reduces the impact on the environment during synthesis 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, I believe this compound will play a more active role in future production and life.

Methyl 3-AMINO-2-PYRAZINE-CARBOXYLATE (10 g, 65.3 mmol) was dissolved in glacial acetic acid (50 mL) by warming to approximately 45oC. To the warm solution was added bromine (3-7 MOL) in acetic acid (5 mL) dropwise and the resulting mixture was stirred at room temperature for 20 minutes. The solution was diluted with water (300 ML) and then stirred at room temperature for 30 minutes, which resulted in a precipitate. The precipitate was then filtered, washed with water and dried to afford methyl 3-AMINO-6-BROMO-2-PYRAZINE-CARBOXYLATE as a yellow solid (14. 2 g, 94 %). IH NMR (300 MHz, CDC13) 63. 99 (s, 3 H), 8.30 (s, 1 H) ; 13C NMR (100 MHZ, CDC13) A 53.02, 123.49, 124.85, 150.24, 154.70, 166.04.

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 2-aminopyrazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN IDEC MA INC.; WO2004/92177; (2004); A1;,
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Synthetic Route of 21948-70-9, A common heterocyclic compound, 21948-70-9, name is 2-Methylthiopyrazine, molecular formula is C5H6N2S, 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.

The mixture of 2-methylthiopyrazine (120 mg, 0.95 mmol) andMeI (203 mg 1.43 mmol) was stirred in a closed vial at 80 C for 2 h.The precipitated orange powder of [MMTP]I was washed withdiethyl ether (2 Chi 8 mL) and dried under vacuum. Yield: 230 mg(90%). 1H NMR (500.13 MHz, CD3CN): delta = 9.03 (dd, JHH = 5.1, 2.8 Hz,1H, C2-H), 8.73 (s, 1H, C5-H), 8.27 (s, 1H, C6-H), 4.25 (s, 3H,Me-N), 2.69 (s, 3H, Me-S). FT-IR (KBr, cm-1): 380 (vs), 420 (w), 449(s), 528 (m), 710 (s), 746 (s), 831 (s), 874 (s), 887 (s), 955 (s), 982 (s),1003 (m), 1124 (s), 1144 (w), 1173 (m), 1221 (vw), 1240 (s), 1260 (s),1281 (s), 1317 (vs), 1439 (m), 1454 (m), 1472 (m), 1528 (s), 1611 (s),2851 (vs), 2916 (vs), 2988 (s), 3028 (s), 3051 (s), 3100 (s). Anal. Calcdfor C6H9IN2S: , 26.88; , 3.38; N, 10.45. Found: , 26.9; , 3.3; N,10.3.

The synthetic route of 21948-70-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Artem’ev, Alexander V.; Bagryanskaya, Irina Yu; Journal of Molecular Structure; vol. 1173; (2018); p. 743 – 749;,
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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. 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, A new synthetic method of this compound is introduced below., category: Pyrazines

(2) To a 100 mL eggplant flask were added the yellow oil (1.65 g) prepared in the above step, 2-chloro-3-hydrazinylpyrazine (1.26 g), and diisopropylethylamine (4.56 mL) under argon gas flow, and the resulting mixture was stirred at 80 C. for 4 hours. (1716) After the reaction was completed, the mixture was concentrated under reduced pressure, water was added thereto, and the resulting mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residues were subjected to silica gel chromatography (hexane:ethyl acetate=70:30 to 50:50) using YAMAZEN medium pressure preparative (Silica L (40 g)), the fractions comprising the target compound (Rf value=0.25 (hexane:ethyl acetate=1:1)) were collected, concentrated under reduced pressure, to the resulting residues was added diisopropyl ether, the precipitated solid was filtered, and dried under reduced pressure to give the title compound (1.53 g) (yield 62%) as a white solid. (1717) MS(CI) m/z: 284/286 [M+H]+

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; MITSUBISHI TANABE PHARMA CORPORATION; UBE INDUSTRIES, LTD.; NAKAJIMA, Tatsuo; HAYASHI, Norimitsu; ISHIZAWA, Kouhei; TSUZAKI, Yasunori; IWAMURA, Ryo; TSUBOIKE, Kazunari; US2019/185479; (2019); A1;,
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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 59489-71-3 as follows. Product Details of 59489-71-3

EXAMPLE 1B 5-amino-2-pyrazinecarbonitrile A mixture of Example 1A (19.29 g, 105 mmol), freshly powdered KCN (16.9 g, 260 mmol), CuI (49.5 g, 260 mmol), 18-crown-6 (2.08 g, 7.8 mmol), and (PPh3)4Pd (1.8 g, 1.57 mmol) in N,N-dimethylformamide (600 mL) was stirred at room temperature for 30 minutes and heated to reflux in an oil bath preheated to about 200 C. The solution was stirred at reflux for 3 hours, cooled to room temperature, poured into ethyl acetate (1 L), filtered through diatomaceous earth (Celite), treated with silica gel (100 g), and concentrated. The concentrate was purified by flash column chromatography on silica gel with 60% ethyl acetate/hexanes to provide 11.9 g (94.4%) of the desired product. MS (APCI(+)) m/z 121 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta 8.40 (d, J=0.7 Hz, 1H), 7.90 (d, J=0.7 Hz, 1H), 7.47-7.69 (br s, 2H).

According to the analysis of related databases, 59489-71-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Li, Gaoquan; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Sham, Hing L.; Wang, Gary T.; US2004/259885; (2004); A1;,
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Pyrazine | C4H4N2 – PubChem

Related Products of 4949-13-7, 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 4949-13-7 as follows.

STEP 1. 2-FLUORO-3-IODOPYRAZINE Butyl lithium solution (2.5 M in hexane, 881 mL, 2.01 mol) and 1.5 L of dry THF were charged into a flame-dried 5.0 L round-bottomed flask. The flask was cooled to -50 C. and 2,2,6,6-tetramethylpiperidine (312.0 mL, 2.20 mol) was added dropwise. The reaction mixture was warmed to 0 C. without taking the cold bath away and kept at that temperature for 20 min. The reaction was then cooled to -78 C., and 2-fluoropyrazine (180 g, 1.84 mol) in 150 mL of THF was added dropwise. The mixture was kept at -78 C. for 5 min. Iodine (464 g, 1.84 mol) in 500 mL of THF was added dropwise and the reaction mixture was kept at -78 C. for 1 h. The reaction was quenched with the addition of 250 mL of concentrated HCl, 250 mL MeOH and 250 mL THF at -78 C. The cold bath was then removed, and aqueous sodium bisulfite was added to get rid of traces of unreacted iodine. The solvent was then evaporated and the residue was diluted with water and adjusted to pH 8. The mixture was extracted with ethyl acetate (3*1.5 L). Combined ethyl acetate layer was dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (Silica:100-200 mess, solvent: 10% EtOAc/hexanes) to give the title compound as a white solid.

According to the analysis of related databases, 4949-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; US2010/160280; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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 486424-37-7, name: 3-Amino-6-bromopyrazine-2-carboxylic acid

Dichlorobis(triphenylphosphine)palladium (H) (0.04 g) was added to a solution of 1 – { 2-[2-methoxy-4-(4,4,5,5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-yl)phenoxy]ethyl Jpyrrolidine (1.26 g), 3-amino-6-bromopyrazine-2-carboxylic acid (0.844 g) and 2M aqueous sodium carbonate solution (2.4 ml) in a 2:7:3:2 mixture of DMF:dimethoxyethane:water:ethanol (30 ml). The reaction mixture was heated to 1600C for 20 minutes in a IOOW microwave oven. The mixture was cooled to ambient temperature and diluted with methanol. The resultant mixture was added to an SCX ion exchange column which was eluted with methanol, followed by 2M methanolic ammonia solution. There was thus obtained 3-amino- 6-[3-methoxy-4-(2-pyrrolidin-l-ylethoxy)phenyl]pyrazine-2-carboxylic acid (1.2 g); Mass Spectrum: M+H* 359; RT 0.79 min.

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; ASTRAZENECA AB; WO2009/7390; (2009); A2;,
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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. 14399-37-2, name is 3,6-Dichloropyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 3,6-Dichloropyrazin-2-amine

To a 200 mL round bottom flask was added NaiS (10.816 g, 44wt% containing crystalline water, 60.978mmol) and toluene (100 mL). The mixture was heated to reflux, and water was removed with a Dean-Stark trap (about 5~6 mL water was distilled out). After cooling, the mixture was concentrated to dryness.[00319] To above round bottom flask was added Y7d (5.000 g, 30.489mmol) and 2- methylbutan-2-ol (50 mL), the reaction was heated to reflux and stirred for 36 h. After cooling to 25 C, the mixture was filtered. The solvent of the filtrate was exchanged with n-heptane (5 V, 3 times, based on Y7d), and finally concentrated to IV residue. THF (25 mL) was charged to the residue at 25 C and stirred. The suspension was filtered and washed with THF/n-heptane (5 mL/5 mL) to give a brown solid (6.200 g). To another 200 mL round bottom flask was added above brown solid (6.200 g),10% brine (25 mL), Me-THF (30 mL) and n-B NBr (9.829 g, 30.489 mmol). The mixture was stirred for 0.5 h at room temperature, and the phases were separated. The organic phase was washed with 20% brine (25 mL), and exchanged the solvent with /.vopropanol (5 V *3 times, based on Y7d) to give the /.Yopropanol solution of Y7c (27.000g, 99.2% purity by HPLC area, 58.08% assay yield). 1H NMR (400 MHz, DMSO-d6) d = 6.88 (s, 1H), 2.97 – 2.92 (m, 14H), 1.38 – 1.31 (m, 14H), 1.13 – 1.04 (m,14H), 0.73 – 0.69 (t, 21H).

The synthetic route of 14399-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FEI, Zhongbo; LU, Gang; WAN, Yinbo; WANG, Jianhua; WU, Quanbing; ZHANG, Hao; (116 pag.)WO2020/65453; (2020); A1;,
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Application of 768-05-8, A common heterocyclic compound, 768-05-8, name is Pyrazinoic acid hydrazide, molecular formula is C5H6N4O, 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.

A solution of 4-[(2,4-dichlorophenyl)carbonyl]-2-piperazinone (I6) (0.273 g, 1 mmol) in dry Dichloromethane (DCM) (3 ml) was stirred at room temperature under argon. Triethyloxonium tetrafluoroborate (0.199 g, 1.050 mmol) was added and the reaction solution was stirred for 10 minutes. 2-pyrazinecarbohydrazide (0.166 g, 1.200 mmol, commercially available) was then added and the solution was stirred for a further 1 hour. The solvent was then concentrated before n-butanol (3.00 ml) was added and the solution was stirred, under reflux and argon, for 4 hours. LCMS confirmed product location, thus the solution was cooled to room temperature before the solvent was evaporated in vacuo. The remaining residue was then purified by flash chromatograpghy (Biotage SP4, 25M cartridge) with a gradient of 0 to 10% 2M NH3/MeOH in DCM. TLC confirmed product location and the solvent from the combined fractions was evaporated in vacuo. The remaining residue was then further purified by mass-directed automated HPLC. The solvent was then evaporated in vacuo, and the remaining solid was triturated with ether, and dried in a vacuum oven to yield the product in 0.137 g.LCMS: m/z = 375 (M+ H)+, retention time = 0.83 minutes (2 minutes). 1H NMR (500 MHz; d6-DMSO) delta 9.37 (1 H, d), 8.75 (1 H, m), 8.74 (1 H, m), 7.79 (1 H, d), 7.61 (1 H, d), 7.57 (1 H, dd), 5.27 (1 H, d), 4.94 (1 H, d), 4.47 (1 H, m), 4.38 (1 H, m), 3.69 (2H, m).

The synthetic route of 768-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (2010); A1;,
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