Category: Pyrazines

These common heterocyclic compound, 912773-24-1, name is 6-Bromoimidazo[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. Product Details of 912773-24-1

Synthesis of 6-bromo-3-iodoimidazo[ 1 ,2-a]pyrazineA degassed solution of 6-bromoimidazo[l,2-a]pyrazine (500 mg, 2.52 mmol) and NIS (852 mg, 3.79 mmol) in DMF (10 mL) was heated to 60 C for 10 hours. The reaction mixture was cooled to RT and extract with DCM. The organics were washed with Na2S203 (aq), brine and dried over Na2S04. After concentrated, the crude product was purified by column (PE : EtOAc = 5 : 1) to obtain 6-bromo-3-iodoimidazo[l,2-a]pyrazine (530 mg, yield: 65%). 1H-NMR (CDC13, 400 MHz) delta 8.75 (s, 1H), 8.18 (s, 1H), 7.82 (s, 1H). MS (M+H)+: 324 / 326.

The synthetic route of 6-Bromoimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCCOMAS, Casey Cameron; LIVERTON, Nigel J.; HABERMANN, Joerg; KOCH, Uwe; NARJES, Frank; LI, Peng; PENG, Xuanjia; SOLL, Richard; WU, Hao; PALANI, Anandan; DAI, Xing; LIU, Hong; HE, Shuwen; DANG, Qung; WO2013/34048; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, 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 63286-28-2, Recommanded Product: 2-Chloro-3-hydrazinylpyrazine

Add trifluoroacetic anhydride to the flask, use ethyl acetate as a solvent, stir in an ice bath, add ethyl acetate to intermediate b (5g, 0.0346mol) and sonicate to mix thoroughly, then slowly add trifluoroacetic anhydride. , Stir in an ice bath, check the progress of the reaction by spotting the plate. After the reaction, the solution was directly extracted with NaOH solution and ethyl acetate, and the organic phase was collected to be rotary-evaporated to obtain an oil. After drying, 10.9 g of a gray solid was obtained with a yield of 93.3%.

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

Reference:
Patent; Jiangxi Science and Technology Normal University; Zhu Wufu; Zheng Pengwu; Xu Shan; Liu Xiaobo; Zhang Qian; Zhou Lingjia; Han Haoyun; Yu Li; Zhou Hualan; Qiu Yufeng; (25 pag.)CN110467616; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 138588-41-7, These common heterocyclic compound, 138588-41-7, name is Pyrazine-2-carboximidamide hydrochloride, 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 mixture of ethyl 3-cycloheptyl-3-oxo-2-(2,4,6-trifluorophenyl)propanoate (649 mg, 1.9 mmol) and 2-pyrazinecarboxamidine hydrochloride (452 mg, 2.85 mmol) in 1.5 mL of tributylamine is stirred under nitrogen atmosphere at 160 C. for 4 h. The mixture is cooled to room temperature and the excess of tributylamine is decanted off. The residue is washed with hexanes and chromatographed over silica gel, eluding with 10% methanol in ethyl acetate. Concentration provides 6-cycloheptyl-2-pyrazin-2-yl-5-(2,4,6-trifluorophenyl)pyrimidin-4-ol as a light yelllow solid. MS: m/z 401.2 (M+H).

The synthetic route of 138588-41-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2005/75357; (2005); 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 1208082-91-0 as follows. HPLC of Formula: C7H5Br2N3

Preparation of Intermediate I-10. A mixture of Intermediate I-05 (1.75 g, 6.015 mmol), morpholine (0.526 mL, 6.015 mmol) and DCM (20 mL) was stirred at it for 16 h. Additional morpholine (0.526 mL, 6.015 mmol) was added and the mixture was stirred at it for 18 h more. Na2CO3 sat. aq. was added. The organic phase was separated, dried (Na2SO4), filtered and evaporated till dryness to obtain 1.8 g of intermediate I-10 (Y: quantitative). The resulting product was used in the next step without further purification.

According to the analysis of related databases, 1208082-91-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Centro Nacional De Investigaciones Oncologicas (CNIO); US2012/83492; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19745-07-4, name is 2,5-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 19745-07-4, category: Pyrazines

Example 9 N-[(1S,2S)-2-[(5-Chloropyrazin-2-yl)amino]cyclopentyl]-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide To a solution of N-[(1S,2S)-2-aminocyclopentyl]-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride (Intermediate 7; 100 mg, 0.31 mmol) in NMP (1.0 ml) was added DIPEA (160 mg, 1.24 mmol) and 2,5-dichloropyrazine (CAS number 19745-07-4; 92 mg, 0.62 mmol). The resulting reaction mixture was stirred and heated under microwave irradiation at 180° C. for 15 minutes. Upon completion, the reaction mixture was poured into water (3 ml) and extracted with ethyl acetate (3*10 ml). The combined organics were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1percent ammonia) to afford the title compound. 1H NMR (DMSO-d6) delta ppm 1.44-1.56 (m, 2H), 1.62-1.68 (m, 2H), 1.92-2.04 (m, 2H), 2.38 (s, 3H), 4.01-4.10 (m, 2H), 7.19 (s, 1H), 7.28-7.30 (m, 1H), 7.39-7.41 (m, 1H), 7.62-7.64 (m, 1H), 7.80-7.81 (s, 1H), 7.93 (s, 2H), 8.03 (s, 1H), 8.35-8.37 (m, 1H) MS ES+: 398

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-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Fieldhouse, Charlotte; Glen, Angela; Maine, Stephanie; Fujimoto, Tatsuhiko; Robinson, John Stephen; US2015/232460; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5521-55-1, These common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, 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 boron trifluoride-diethyl ether complex (91.7 muL) was added dropwise to a suspension of 2-methylpyrazine-5-carboxylic acid (1 g) and tert-butyl 2,2,2-trichloroacetimidate (4.75 g) in THF (20 mL) under ice-cooling. The reaction solution was warmed to RT, followed by stirring for 2 h. A saturated NaCl solution and EtOAc were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous MgSO4, and the insoluble matter was separated by filtration. The filtrate was concentrated and purified by silica gel column chromatography to obtain the title compound (1.4 g). 1H-NMR (CDCl3) delta (ppm): 1.65 (s, 9H), 2.65 (s, 3H), 8.57 (d, J=1.2 Hz, 1H), 9.10 (d, J=1.6 Hz, 1H).

Statistics shows that 5-Methylpyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 5521-55-1.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; US2012/190672; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 109-08-0,Some common heterocyclic compound, 109-08-0, name is 2-Methylpyrazine, molecular formula is C5H6N2, 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.

Compound 17: (E)-2-[2-(Pyrazin-2-yl)vinyl)benzamide hydrochloride: n-Butyl lithium (2.5 M in hexanes, 4.8 mL, 12.0 mmol, 1.2 eq.) was added dropwise to a solution of diisopropylamine (1.83 mL, 1.32 g, 13.0 mmol, 1.3 eq.) in dry tetrahydrofuran (25 mL) at -78 °C. The mixture was stirred at -78 °C for 10 min and 2-methylpyrazine (0.91 mL, 0.94 g, 10.0 mmol, 1.0 eq.) was added dropwise. The resulting mixture was stirred at -78 °C for 30 min. A solution of 2-cyanobenzaldehyde (1.31 g, 10.0 mmol, 1.0 eq.) in dry THF (10 mL) was added dropwise and the mixture was allowed to slowly warm up to room temperature over 2 h while stirring. The reaction was quenched by addition of water (20 mL). The pH was adjusted to -10 by careful addition of cone. HCl and the mixture was extracted with dichloromethane (3 x 25 mL). The combined organic extracts were washed with brine (25 mL), dried over sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (SiO2, 1:9 methanol-ethyl acetate) providing 2-(1-hydroxy-2-(pyrazin-2-yl)ethyl)benzamide (1.06 g, 44percent yield) as a clear yellow oil. 1,8-Diazabicyclo[5.4.0]undec-7-ene (1.61 mL, 1.69 g, 11.1 mmol, 2.5 eq.) was dropwise to a stirred solution of 2-[1-hydroxy-2-(pyrazin-2-yl)ethyl]benzamide (1.00 g, 4.4 mmol, 1.0 eq.) in dichloromethane (25 mL). The mixture was stirred at room temperature for 16 h. Water (25 mL) was added and the layers were separated. The aqueous layer was extracted with dichloromethane (2 x 25 mL) and the combined organic extracts washed with brine (25 mL), dried over sodium sulfate and concentrated in vacuo. The residue was taken up in ethyl acetate (20 mL) and filtered. The solids were washed with ethyl acetate (2 x 5 mL) and dried in vacuo providing (E)-2-[2-(pyrazin-2-yl)vinyl]benzamide (0.21 g, 21percent yield) as a fine off-white solid. A solution of hydrochloric acid (2.0 M in diethyl ether, 0.53 mL, 1.07 mmol, 1.2 eq.) was added dropwise to a stirred suspension of (E)-2-[2-(pyrazin-2-yl)vinyl]benzamide (0.20 g, 0.09 mmol, 1.0 eq.) in dry diethyl ether (7.5 mL). The mixture was stirred at room temperature for 1 h and was filtered. The solids were washed with diethyl ether (2 x 5 mL) and dried in vacuo providing (E)-2-[2-(pyrazin-2-yl)vinyl]benzamide hydrochloride (0.20 g, 86percent yield) as a fine yellow solid; 1H NMR (400 MHz, DMSO-d6) delta 7.33-7.55 (m, 5H, 2Ar+NH2+C=CH), 7.88-7.96 (m, 2H, Ar), 8.11 (d, J = 16.0 Hz, 1H, C=CH), 8.51 (s, 1H, Ar), 8.64 (s, 1H, Ar), 8.71 (s, 1H, Ar).

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

Reference:
Patent; UNIVERSITY COLLEGE DUBLIN – NATIONAL UNIVERSITY OF IRELAND, DUBLIN; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH, NEAR DUBLIN; KENNEDY, Breandan; REYNOLDS, Alison; O’SULLIVAN, Jacintha; BAXTER, Andrew, Douglas; WO2015/107122; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, 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 55557-52-3, Recommanded Product: 55557-52-3

Intermediate 1 (S)-Benzyl 2-(8-amino-1-bromoimidazo[1 ,5-alpyrazin-3-vnpyrrolidine-1-carboxylate (a) (3-Chloropyrazin-2-yl)methanamine. hydrochloride To a solution of 3-chloropyrazine-2-carbonitrile (160 g, 1 .147 mol) in acetic acid (1.5 L) was added Raney Nickel (50% slurry in water, 70 g, 409 mmol). The resulting mixture was stirred under 4 bar hydrogen at room temperature overnight. Raney Nickel was removed by filtration over decalite and the filtrate was concentrated under reduced pressure and co-evaporated with toluene. The remaining brown solid was dissolved in ethyl acetate at 50C and cooled on an ice-bath. 2M hydrogen chloride solution in diethyl ether (1 .14 L) was added in 30 min. The mixture was allowed to stir at room temperature over weekend. The crystals were collected by filtration, washed with diethyl ether and dried under reduced pressure at 40C. The product brown solid obtained was dissolved in methanol at 60C. The mixture was filtered and partially concentrated, cooled to room temperature and diethyl ether (1000 ml) was added. The mixture was allowed to stir at room temperature overnight. The solids formed were collected by filtration, washed with diethyl ether and dried under reduced pressure at 40C to give 153.5 g of (3-chloropyrazin-2- yl)methanamine. hydrochloride as a brown solid (74.4 %, content 77 %).

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; MSD OSS B.V.; BARF, Tjeerd A.; JANS, Christiaan, Gerardus, Johannes, Maria; MAN, de Adrianus, Petrus, Antonius; OUBRIE, Arthur A.; RAAIJMAKERS, Hans C.A.; REWINKEL, Johannes, Bernardus, Maria; STERRENBURG, Jan-Gerard; WIJKMANS, Jacobus C.H.M.; WO2013/10868; (2013); 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. 2727-13-1, name is 3-Amino-6-chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Computed Properties of C5H4ClN3O2

To a mixture of 3-amino-6-chloropyrazine-2-carboxylic acid (1 .00 g; 5.76 mmol) and triethylamine (2.40 ml; 17.3 mmol) in abs. DMF is added 2-tert-butyl-5-methyl-1 ,2-oxazol-2- ium hexafluoro-phosphate (4.93 g; 17.3 mmol). The mixture is stirred at r.t. over night. Ice- water is added. The supernatant is decanted from the resin-like product which is sufficiently pure to be further reactedESI Mass spectrum: m/z = 313 [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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; KLEY, Joerg; HAERLE, Daniel; LINZ, Guenter; STEHLE, Sandra; WO2013/64451; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 55557-52-3, The chemical industry reduces the impact on the environment during synthesis 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, I believe this compound will play a more active role in future production and life.

[A] 1H-Pyrazolo [34-b] pyrazin-3-amine[0304][0305]To a stirred solution of 3-chloropyrazine-2-carbonitrile (5 g 35.8 mmol) in EtOH (100 mL) was added N2H4. H2O (85aq. 21 g 360 mmol) dropwise at 15 . After the addition the reaction mixture was allowed to warm up and stirred at 110 for 16 h. After cooling to room temperature the solvent was removed under reduced pressure and the residue solid was washed with EtOH (20 mL) to give a crude title compound (3 g 62yield) as a brown solid. MS 136.1 [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, 3-Chloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; TAN, Xuefei; WANG, Lisha; CUMMING, John Graham; LIU, Yongfu; WU, Jun; LI, Dongbo; SHEN, Hong; SHI, Tianlai; (179 pag.)WO2017/133657; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem