Tag: M.W=100-200

These common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]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. Recommanded Product: 2-Bromo-5H-pyrrolo[2,3-b]pyrazine

2-bromo-5H-pyrrolo[2,3-b]pyrazine (6.5g, 32.82 mmol), (4- isopropylsulfonylphenyl) boronic acid (7.859 g, 34.46 mmol) and palladiumtriphenylphosphane complex (1.896 g, 1.641 mmol) were combined in a round bottomed flask. To this mixture was added dioxane (97.50 mL) and then an aqueous solution of Na2C03 (49.23 mL of 2 M, 98.46 mmol). The resulting suspension was stirred at 100 C overnight, then heating was stopped and water added. The resultant precipitate was collected and dried in vacuo at 40C, to give the sub-title compound as a brown solid (9.45 g, 95% yield). XH NMR (400.0 MHz, DMSO) d 12.25 (s, 1H), 9.00 (s, 1H), 8.43 (d, J = 8.4 Hz, 2H), 7.99 – 7.96 (m, 3H), 6.74 (d, J = 3.5 Hz, 1H), 3.57 (s, 1H) and 1.20 (d, J = 6.8 Hz, 6H) ppm; MS (ES+) 435.2

The synthetic route of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; EVERITT, Simon; MORTIMORE, Michael, Paul; CHARRIER, Jean-damien; MACCORMICK, Somhairle; STORCK, Pierre-henri; KNEGTEL, Ronald; PINDER, Joanne; DURRANT, Steven; WO2012/178124; (2012); 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, Computed Properties of C5H2Cl2N2O2

[0731] To a solution of 146A (10 g, 51.82 mmol) and HATU (21.67 g, 57 mmol) in DMF (50 mL), DIEA (19.86 mL, 114 mmol) was added to the solution. After 30 minutes, N,Odimethylhydroxyamine hydrochloride (6.09 g, 62.18 mmol) was added to the solution. The mixture was stirred for overnight. 300 mL of water was added and extracted with EtOAc three times (100 mL). The crude product was purified by flash column to provide the desired product. MS (m/z) 236 [M+H].

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; GILEAD SCIENCES, INC.; BRIZGYS, Gediminas; CANALES, Eda; CHOU, Chien-hung; GRAUPE, Michael; HU, Yunfeng, Eric; LINK, John, O.; LIU, Qi; LU, Yafan; SAITO, Roland, D.; SCHROEDER, Scott, D.; SOMOZA, John, R.; TSE, Winston, C.; ZHANG, Jennifer, R.; WO2014/134566; (2014); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 54608-52-5, 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.

To a mixture of 2-hydrazinylpyrazine (0.551 g, 5.00 mmol) and ethyl 2-cyanopropanoate (0.669 g, 5.00 mmol) in abs. EtOH (10 mL) was added 3M NaOEt in EtOH (0.167 mL, 0.501 mmol) and the mixture was heated at reflux for 64 hours. The mixture was concentrated and the residual yellow-brown solid was treated with EtOAc (30 mL) and sonicated. The resulting tan suspension was stirred vigorously for 8 hours. The solid was collected via vacuum filtration, washed with EtOAc and dried in vacuum to afford the title compound as a light tan powder (682 mg, 71%). 1H NMR (DMSO de) delta 10.3 (br s, 1H), 8.82 (s, 1H), 8.30 (d, 2H), 6.55 (s, 2H), 1.71 (s, 3H).

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

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; ANDREWS, Steven, Wade; BLAKE, James, F.; BRANDHUBER, Barbara, J.; HAAS, Julia; JIANG, Yutong; KERCHER, Timothy; KOLAKOWSKI, Gabrielle, R.; THOMAS, Allen, A.; WINSKI, Shannon, L.; WO2014/78454; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 89123-58-0, The chemical industry reduces the impact on the environment during synthesis 89123-58-0, name is 5-Bromopyrazine-2,3-diamine, I believe this compound will play a more active role in future production and life.

Oxalyl chloride (3ml) was added to a solution of 5-({5-chloro-2-[(2-methylpropyl)oxy]- phenyl}methyl)-2-furancarboxylic acid (3.09g, lOmmol) and one drop of DMF in dichloromethane (30ml) and left at room temperature for one hour. The resulting solution was evaporated to dryness, azeotroped with toluene and the residue dissolved in dichloromethane (15ml) and added dropwise to a stirred solution of 2,3-diamino-5- bromopyrazine (2.08g, 11mmol) and 4-dimethyaminopyridine (100mg, 0.82mmol) in pyridine (20ml) and stirred for one hour. The solution was evaporated and the residue dissolved in ether/water. The organic phase was dried with magnesium sulphate, evaporated and chromatographed on silica gel eluting with ethyl acetate/hexane (15:85) to give 3.35g of white solid which was dissolved in acetic acid (40ml) and stirred and refluxed for 5 days. The resulting solution was evaporated, dissolved in ethyl acetate and washed with 2M sodium hydroxide solution. The organic phase was dried with magnesium sulphate, evaporated and purified by flash chromatography on silica eluting with ethyl acetate/hexane (1 :3) to give a pale yellow solid. A sample was dissolved in methanol/dichloromethane and hydrogen chloride in ether (1ml) was added. The solvent was evaporated and the residue triturated with ether and filtered off to give the title compound as a solid. LC/MS: Rt=3.67, [MH]+ 463.11 , 464.16.

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, 5-Bromopyrazine-2,3-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/114272; (2006); 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. 89283-32-9, name is (3-Chloropyrazin-2-yl)methanol, A new synthetic method of this compound is introduced below., Quality Control of (3-Chloropyrazin-2-yl)methanol

Under nitrogen protection,To a solution of 3-chloro-2-pyrazine methanol (60 g, 414.9 mmol)Triphenylphosphine (130.4 g, 497.9 mmol)And phthalimide (73.2 g, 497.9 mmol)Of the 500 mL THF solution,Was slowly added dropwise at -5 DIAD (100.6g, 497.9mmol),After complete addition, the reaction mixture was stirred at 20 3h,TLC shows that after completion of the reaction,Water was added to the reaction mixture and then extracted with EA (1 L x 3)The organic phase was dried sufficiently with anhydrous Na2SO4,After evaporation in vacuo, the residue was purified by flash chromatography (PE / EA = 30/1)To give 90.8 g of the title compound

The synthetic route of 89283-32-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Beite Pharmaceutical Co., Ltd.; Chengdu Hai Borui Pharmaceutical Co., Ltd.; Li Yingfu; Huang Haoxi; Liu Guanfeng; Chen Tonghun; Ren Junfeng; Su Zhonghai; (96 pag.)CN106831787; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 140914-89-2, A common heterocyclic compound, 140914-89-2, name is 2-(Pyrazin-2-yl)acetic acid, molecular formula is C6H6N2O2, 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 34 (300 mg, 0.75 mmol), 2-(pyrazin-2-yl)acetic acid (120 mg, 0.87 mmol), HATU (600 mg, 1.59 mmol), N-Ethyldiisopropyl amine (0.3 ml, 2.17 mmol) were dissolved in DMF (4 ml). This mixture was stirred at rt for 1 h. Reaction mass was poured in to water to obtain a solid. Solid was filtered and purified the solid by column chromatography on 60-120 silica gel using MeOH and DCM (5:95) as eluent to afford the titled compound (13 mg) as a Pale-brown solid. M.P.: 232-234C. JH-NMR (delta ppm, DMSO-<, 400 MHz): 12.74 (s, 1H), 10.90 (s, 1H), 8.65 (s, 1H), 8.57-8.52 (m, 2H), 7.98 (d, J 9.8, 1H), 7.40-7.36 (m, 2H), 7.35-7.25 (m, 1H), 7.18- 7.12 (m, 2H), 4.30 (d, J 13.3, 2H), 4.06 (s, 2H), 3.79 (s, 2H), 3.40-3.31 (m, 1H), 3.05 (t, J 12, 2H), 2.10 (d, J 10.7, 2H), 1.80-1.66 (m, 2H). The synthetic route of 140914-89-2 has been constantly updated, and we look forward to future research findings. Reference:
Patent; RHIZEN PHARMACEUTICALS SA; BHAVAR, Prashant Kashinath; VAKKALANKA, Swaroop Kumar Venkata Satya; VISWANADHA, Srikant; SWAROOP, Merikapudi Gayatri; BABU, Govindarajulu; WO2015/101957; (2015); A2;,
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. 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 6-Chloropyrazine-2-carboxylic acid

Example 25; N-(tert-Butyl)-6-chloropyrazine-2-carboxamide Thionyl chloride (1 mL, 13. 7 mmol) was added to a suspension of the acid (325 mg, 2 mmol) in toluene (5 mL). A drop of DMF was then added and after stirring at RT for 10 min. the mixture was heated at reflux for lh. The reaction was cooled to RT and toluene and excess thionyl chloride were removed under reduced pressure. Toluene (1 mL) was then added to the residue and this was removed under reduced pressure. This process was repeated, and then CtiCIz (10 mL) was added and the resulting solution cooled to QC. t-Butylamine (0. 45 mL, 4.3 mmol) and triethylamine (1.1mL, 8.0 mmol) were then added and the solution stirred at RT overnight. The solution was diluted with 10 mL) and H20 (10 mL) and the organic layer collected and washed with aq. Na2CA and then dried (Na2SO4). The solvent was removed in vacuo and flash chromatography of the residue using CH2Cl2-MeOH (95: 5) separated the pure product as an oil (290 (at) mg, 68 %).

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; CYTOPIA RESEARCH PTY LTD; WO2005/66156; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 98-97-5, name is Pyrazine-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 98-97-5, COA of Formula: C5H4N2O2

To a solution containing 2-pyrazine carboxylic acid (10 g, 80.5 mmol) in dichloromethane (150 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride EDC (18.5 g, 96.6 mmol) and 1-hydroxybenzotriazole HOBT (13.05 g, 96.6 mmol) and the resulting solution stirred at 25 C. for 30 minutes. Then 1-cyclohexylglycine methyl ester (16.7 g, 80.5 mmol) and Hunig’s base (31.24 g, 241 mmol) was added and the reaction mixture stirred for 2 hours. The reaction mixture was partitioned between water and dichloromethane. The organic layer was removed and dried over MgSO4, filtered and concentrated in vacuo and purified via flash chromatography using ethyl acetate/hexane (20/80 to 30/70) to give a foam (13.3 g, 60%). The product of the previous reaction (6.54 g, 24 mmol) was dissolved in ethanol and treated with 1N sodium hydroxide (35.4 mL, 35.3 mmol) at 25 C. for 4 hours. The mixture was neutralized with 10% HCl to pH 4 and extracted with dichloromethane. The organic layer was removed and dried over MgSO4, filtered and concentrated in vacuo to afford a foam (5 g, 81%).

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

Reference:
Patent; Abbott Laboratories; US2010/29686; (2010); 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. 19847-12-2, name is Pyrazinecarbonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C5H3N3

Pyrazine-2-carbonitrile (10.5 g, 100 mmol) was dissolved in PhMe (100 mL) at 0 C. and 4-chlorophenyl magnesium bromide (100 ml, 1.0 M in Et2O, 100 mmol) was added portion-wise over 5 min. The reaction mixture was stirred for 6 h and NaBH4 (7.58 g, 201 mmol) and tBuOH (100 mL) were added. The reaction mixture was warmed to 60 C. for 18 h and quenched with 1 M aq NaOH solution. The aqueous layer was extracted with EtOAc and the combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (DCM:EtOH:NH3 200:8:1 to 50:8:1) to give the title compound as a brown oil (7.46 g, 34%). MS (ESI+) m/z=220.0 (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; PROXIMAGEN LIMITED; Evans, David; Carley, Allison; Stewart, Alison; Higginbottom, Michael; Savory, Edward; Simpson, Iain; Nilsson, Marianne; Haraldsson, Martin; Nordling, Erik; Koolmeister, Tobias; US2013/102587; (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. 20737-42-2, name is 3-Oxo-3,4-dihydropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Product Details of 20737-42-2

EXAMPLE 67 3-Hydroxypyrazine-2-carboxylic acid is converted to the methyl ester and the ester is reduced with lithium aluminium hydride in tetrahydrofuran to give 3-hydroxy-2-hydroxymethylpyrazine.

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; Smith Kline & French Laboratories Limited; US3950333; (1976); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem