Pyrazines

Electric Literature of 710322-57-9,Some common heterocyclic compound, 710322-57-9, name is Methyl 5-formylpyrazine-2-carboxylate, molecular formula is C7H6N2O3, 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.

To a solution of methyl 5-formylpyrazine-2-carboxylate (2.47 g) in THF (20 mL) was added sodium borohydride (170 mg) portionwise over 10 mins. After stirring for 1 h, methanol (10 mL) was added. The reaction mixture was stirred for a further 20 mins, and then HCl (1 N, aq., 20 mL) and brine (20 mL) were added. The mixture was extracted with EtOAc (3×40 mL) and the combined organic portions dried over MgSO4 and evaporated to afford the title compound (1.31 g). 1H NMR (400 MHz, CDCl3) delta ppm 4.07 (s, 3H), 4.98 (br. s., 2H), 8.80 (s, 1H), 9.27 (s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-formylpyrazine-2-carboxylate, its application will become more common.

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

19745-07-4, 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. 19745-07-4, name is 2,5-Dichloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of Intermediate 2 (0.2 g, 0.74 mmol) in DMF (5 mL,), TEA (0.5 mL,, 3.70 mmol) and 2,5-dichloro pyrazine (0.11 g, 0.74mmol) was added and stirred at 120°C for 2 h. The reaction mixture was concentrated under vacuum and the resulting crude product was dissolved in DCM. It was washed with water, dried over anhydrous Na2SO4, and concentrated under vacuum. The crude product was purified by flash chromatography to afford the title compound (brown oil). 1H NMR (400 MHz, DMSO-d6): delta 8.23 (s, 1H), 7.81 (s, 1H), 6.88 (d, J = 1.2 Hz, 1H), 6.84 (d, J = 8.0 Hz, 1H), 6.74 (dd, J = 1.6, 8.0 Hz, 1H), 5.97 (s, 2H), 3.54-3.52 (m, 4H), 3.39-3.37 (m, 1H), 2.45-2.44 (m, 2H), 2.39-2.37 (m, 2H), 1.27 (d, J = 6.4Hz, 3H). LCMS: (Method A) 347.0 (M+H), Rt. 3.03 min, 97.9percent (Max). HPLC: (Method A) Rt. 3.05 min, 97.6percent (Max).

The synthetic route of 19745-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASCENEURON SA; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; (243 pag.)WO2016/30443; (2016); 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. 5049-61-6, name is Pyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. category: Pyrazines

Aminopyrazine (10 g, 10.5 MMOL) was dissolved in dry DIMETHYLFORMAMIDE (60 ml) and was treated with N-CHLOROSUCCINIMIDE (15.36 g, 11.5 MMOL) under argon at 0 C. The mixture was stirred for 30 minutes and then allowed to warm to room temperature. The mixture was poured onto water and extracted with diethyl ether. The diethyl ether layers were combined and evaporated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of ethyl acetate : pentane (1: 9) to afford the title compound (1.40 g) ;’H NMR (CDC13) 8.02 (1 H, S), 7.76 (1H, s), 4.61 (2H, s).

The synthetic route of 5049-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/56369; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 312736-49-5, name is 3,5-Dichloropyrazine-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 312736-49-5, name: 3,5-Dichloropyrazine-2-carboxylic acid

To a solution of 3,5-dichloropyrazine-2-carboxylic acid (0.304 g, 1.58 mmol) in MeOH (5 mL) and diethyl ether (5 mL) at room temperature was added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, 4.00 mL, 8.00 mmol). The reaction mixture was stirred at RT for 30 min and concentrated. Purification by flash column chromatography on silica gel (5% to 20% EtOAc in hexanes) gave methyl 3,5- dichloropyrazine-2-carboxylate (0.312 g, 1.51 mmol, 96%o yield) as a white solid. LC/MS (ESf) m/z = 207.0 (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, 3,5-Dichloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; MINATTI, Ana Elena; LOW, Jonathan, D.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BROWN, James; FROHN, Michael, J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul, E.; LOPEZ, Patricia; MA, Vu Van; NISHIMURA, Nobuko; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert, M.; SHAM, Kelvin; SMITH, Adrian, L.; WHITE, Ryan; XUE, Qiufen; WO2014/138484; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 113305-94-5, name is 5-Aminopyrazine-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 113305-94-5, Quality Control of 5-Aminopyrazine-2-carbonitrile

To a solution of 5-aminopyrazine-2-carbonitrile (0.6 g, 4.99 mmol) in dry EtOH (9 mL) were added sodium bromide (0.257 g, 2.49 mmol) and chloroacetone (2.01 mL, 24.95 mmol) portionwise. The reaction mixture was heated at 80C for 16 h with stirring, then allowed to cool to r.t. The solvent was removed in vacuo, then the solids were taken up in DCM (100 mL) and washed with saturated aqueous NaHC03 solution (50 mL).The phases were separated and the aqueous phase was extracted with DCM (2 x 50 mL).The combined organic layers were washed with brine (50 mL), then dried (MgS04), filtered and concentrated. Purification by column chromatography, eluting with EtOAc/ heptane (20-100%>), yielded the title compound (220 mg, 28%).

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; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHOVATIA, Prafulkumar Tulshibhai; FOULKES, Gregory; JOHNSON, James Andrew; JONES, Severine Danielle; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LOKE, Pui Leng; LOWE, Martin Alexander; MANDAL, Ajay; NORMAN, Timothy John; PALMER, Christopher Francis; PEREZ-FUERTES, Yolanda; PORTER, John Robert; SMYTH, Donald; TRANI, Giancarlo; UDDIN, Muhammed; ZHU, Zhaoning; (207 pag.)WO2016/198400; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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 C6H6N2O2

General procedure: Under Argon, a stirred solution of carboxylic acid (0.37 mmol,1.0 eq.) and Et3N (0.48 mmol, 1.3 eq.) in dry THF (7 mL) was cooledto 10 C. Ethyl chloroformate (0.55 mmol, 1.5 eq.) was drop wiseadded and the resulting mixture was stirred for 2 h. Afterwards, asolution of sodium azide (0.63 mmol, 1.7 eq.) in water (2 mL) wasadded in one portion. After 1 h at 10 C, the reactionwas found tobe complete (TLC) and was quenched into iced water (5 mL). Themixture was extracted with EtOAc (3 10 mL) and the combinedorganic layers were successively dried over MgSO4, filtered andevaporated. The crude acyl azide was placed in dry toluene (20 mL)and heated at reflux for 1 h to give the corresponding crude isocyanate.The latter was placed in dry dioxane (7 mL) prior to addingthe appropriate amine 8, 9 or 10 (0.37 mmol, 1.0 eq.). The solutionwas heated at 100 C for 24 h. The reaction mixture was cooled andthe volatiles were removed to dryness in vacuum at 40 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5521-55-1, its application will become more common.

Reference:
Article; Boulahjar, Rajaa; Ouach, Aziz; Bourg, Stephane; Bonnet, Pascal; Lozach, Olivier; Meijer, Laurent; Guguen-Guillouzo, Christiane; Le Guevel, Remy; Lazar, Said; Akssira, Mohamed; Troin, Yves; Guillaumet, Gerald; Routier, Sylvain; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 274 – 287;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 5049-61-6, These common heterocyclic compound, 5049-61-6, name is Pyrazin-2-amine, 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 5-bromopyrazin-2-amine To a stirred solution of pyrazin-2-amine (3 g, 31.545 mmol) in anhydrous DCM (30 mL) was added NBS (5.6 g, 31.54 mmol) under nitrogen and stirred at 0 C. for 1 h. Progress of reaction was monitored by TLC. After reaction completion DCM was added and washed with water. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. Crude was purified by silica gel (100-200 mesh) column chromatography using 70% DCM/hexane to 10% ethyl acetate in hexane as eluent to yield 5-bromopyrazin-2-amine (3.4 g, 62.9%) as white solid. MS: 175.1 [M++1]

The synthetic route of 5049-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mankind Pharma Ltd.; Patil, Rakesh Ishwar; Verma, Jeevan; Shah, Dharmesh; Ali, Sazid; Bapuram, Srinivasa Reddy; Rai, Santosh Kumar; Kumar, Anil; (146 pag.)US2017/291910; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 77112-52-8, These common heterocyclic compound, 77112-52-8, name is Ethyl imidazo[1,2-a]pyrazine-2-carboxylate, 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.

10% Pd/C (40 mg) was added to a solution of ethyl imidazo[1,2-a]pyrazine-2-carboxylate (410 mg, 2.15 mmol) and conc.HCl (0.5 mL) in EtOH (9.5 mL) and stirring was continued under a hydrogen atmosphere for 16 h. The reaction mixture was filtered over a celite bed and the filtrate was concentrated under reduced pressure to afford the crude product, which was purified by washing with diethyl ether and dried to afford 400 mg of the title compound as a yellow hygroscopic solid. MS (ESI): m/z 196 (M+H).

The synthetic route of 77112-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; Sasmal, Pradip Kumar; Ahmed, Shahadat; Prabhu, Ganesh; Tehim, Ashok; Paradkar, Vidyadhar; Dattatreya, Marahanakuli Prasanna; Mavinahalli, Nanjegowda Jagadeesh; US2015/5280; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 40155-47-3, name is 3-Methoxypyrazine-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. Product Details of 40155-47-3

[0423] A solution of 3-amino-4-(4-(2,4-difluorophenoxy)piperidin-l-yl)benzonitrile (50 mg, 0.152 mmol), 3~niethoxypyrazme-2-carboxyiie acid (46.8 mg, 0.304 mmol), HATU (115 mg, 0.304 mmol) and DIPEA (106 mu,, 0.607 mmol) in DMF (759 muEpsilon) was stirred on a hot plate at 80C overnight. The reaction mixture was filtered through a Millipore filter, diluted with DMF and MeOH, and purified by HPLC (Shimadzu) eluting with a gradient of ACN in water (basic mode) to give the title compound as a light brown solid (68.7 mg, 97%). .H NMR (400 MHz, CDCb) delta ppm 2.07 – 2.18 (m, 2 H), 2.19 – 2.28 (m, 2 H), 2.91 (ddd, J=l 1.68, 8.02, 3.28 Hz, 2 H), 3.26 (ddd,./ 1 1.62. 7.58, 3.54 Hz, 2 H), 4.18 (s, 3 H), 4.37 – 4.45 (m, 1H), 6.78 ·· 6.86 (m, 1H), 6.90 (ddd,.7=11, 12, 8.34, 3.03 Hz, 1H), 7.03 (td,.7=9.09, 5,56 Hz, 1H), 7.23 (d,.7=8,34 Hz, 1H), 7.41 (dd, J=8.34, 2.02 Hz, 1H), 8.26 (d, J=2.27 Hz, 1H), 8.41 (d, J=2.53 Hz, 1H), 8.93 (d,./ 1.77 Hz, 1H), 10.62 (s, 1H); ESI-MS m/z [M+H}+ 466.2.

The synthetic route of 3-Methoxypyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); 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. 5049-61-6, name is Pyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., name: Pyrazin-2-amine

A solution of aminopyrazine (1 g, 10.5 mmol) and chloroacetaldehyde (50% wt in H2O; 1.98 g, 12.6 mmol) in 1.6 mL of EtOH was heated at 900C in a sealed tube for 5 h. Upon cooling to ambient temperature, the reaction mixture was concentrated and diluted with dichloromethane (DCM). The organic layer washed with saturated aqueous NaHCO3 then dried over MgSO4 and concentrated. The crude product was purified by silica gel flash chromatography (eluted with 10% MeOH/DCM) to provide 0.8 g of product.

According to the analysis of related databases, 5049-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; WO2007/75869; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem