Category: 6966-01-4

Electric Literature of 6966-01-4, A common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, 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.

4- (PYRROLIDIN-1-YLSULFONYL) phenylboronic acid (0.33 g, 1.29 mmol), methyl 3-AMINO-6- bromopyrazine-2-carboxylate (0.25 g, 1.08 mmol; described in: H. Ellingson, J. Amer. CLIENT. Soc. 1949, 2798), K3PO3 (3 M, 1.1 ML, 3.2 mmol), and Pd (dppf) C12 (0.044 g, 54 , UMOL) were suspended in ethylene glycol dimethyl ether/water (1.5 : 0.5 mL) and heated in a microwave oven at 160 C for 10 min. The reaction was repeated 3 times. The combined product mixtures were evaporated with silica gel and the crude product was purified by chromatography on silica gel using a heptane to ethyl acetate gradient to give 0.96 g (82% yield) of the title compound: MS (ES) NAL, Z 363 (M++1).

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; ASTRAZENECA AB; WO2004/55006; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6966-01-4,Some common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, 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 methyl 3-amino-6-bromopyrazine-2-carboxylate (500 mg, 2.16 mmol), tetrakis(triphenylphosphine)palladium(0) (124 mg, 0.108 mmol) and sodium methanethiolate (306 mg, 4.31 mmol) in DMF (10 ml) was sealed in a nitrogen flushed pressure tube. The pressure tube was heated at 50 C for 2 h then allowed to cool to RT. The reaction mixture was diluted with EtOAc (30 ml) then washed with hydrochloric acid (1 M, 2 x 25 ml). A precipitate formed, which was removed by filtration. The filtrate was dried over MgS04 and evaporated. The crude material thus obtained was purified by flash column chromatography on C18 (60 g). The column was eluted with MeC iHiO + 0.1% formic acid using the following gradient (%MeCN, column volumes): 10%, 2 CV; 10-100%, 20 CV; 100%, 2 CV. The desired fractions were combined and evaporated to yield the product as a dark yellow solid (77 mg, 19%).1H NMR (250 MHz, DMSO-de) delta 12.89 (s, 1 H), 8.24 (s, 1 H), 7.25 (s, 2H), 3.30 (s, 3H). LC/MS (System A): m/z (ESI+) = 186 [MH+], Rt = 0.72 min, UV purity = 98%.

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); 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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-amino-6-bromopyrazine-2-carboxylate

Triisopropyl borate (2.7 mL, 11.6 mmol) was added to a solution of 1- [ (4- bromophenyl) SULFONYL]-4-METHYLPIPERAZINE in (1.24 g, 3.87 mmol; described: in Keasling, H. H. et el. J. Med. Chem. 1965, 8, 548-550) in anhydrous tetrahydrofuran (25 mL) at-78 C under an atmosphere of nitrogen, followed by dropwise addition of n-butyllithium (9.8 mL, 15.5 mmol). The resulting mixture was stirred at-78 C for 30 min, then allowed to warm to room temperature. HCl (3 M aq, 7.8 mL, 23.2 mmol) was added and the mixture was stirred at room temperature for 10 min. Sodium carbonate (4.1 g, 38.7 mmol) was added followed by the addition of methyl 3-amino-6-bromo-2-pyrazinecarboxylate (0.79 g, 3.4 mmol; described in: H. Ellingson, J. Amer. Chem. Soc. 1949,2798) and Pd (dppf) Cl2 (95 mg, 0.12 mmol). The resulting mixture was heated at 55 C overnight. Silica was added, the solvent was evaporated and the crude mixture was purified by column chromatography on silica using CHLOROFORM/METHANOL, (99: 1), as the eluent to give 0.923 g (69% yield) of the base as a yellow solid : 1HNMR (DMSO-D6) S 9.0 (s, 1 H), 8.22 (d, J = 7 Hz, 2 H), 7.80 (d, J = 7 HZ, 2 H), 7.62 (BR S, 2 H), 3.90 (s, 3 H) 2.91 (m, 4 H), 2.36 (m, 4 H), 2.12 (s, 3 H); 13CNMR (DMSO-D6) 8 166. 2,155. 1,145. 8,140. 33,127. 5,134. 0,128. 1, 125.7, 109.1, 53.5, 52.3, 45.7, 45.2 ; MS (ESP) M/Z 392 (M++1).

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; ASTRAZENECA AB; WO2004/55006; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, 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 6966-01-4, Application In Synthesis of Methyl 3-amino-6-bromopyrazine-2-carboxylate

Palladium acetate (0.145 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium complex with DCM (0.702 g) were dissolved in DMF (65 ml) and heated to 50 C for 15 minutes. After cooling to room temperature 3-amino-6-bromo-pyrazine-2-carboxylic acid methyl ester (5.0 g), 4-fluoro-phenyl boronic acid (3.82 g) and triethylamine (4.5 ml ) were added and the mixture heated to 90 C for 20 hours with stirring. The solvent was evaporated and the residue dissolved in DCM. The organic phase was washed with dilute ammonium hydroxide solution and water. After drying with sodium sulphate and filtration the solvent was evaporated and the residue purified by column chromatography on silica gel eluting with hexane: ethyl acetate, 3: 1 to give 3-amino-6-(4-fluorophenyl)-pyrazine-2- carboxylic acid methyl ester (0.670 g). ‘H NMR (CDCI3) 8 ppm: 3.92 (s, 3H), 6.4 (bs,1H), 7.1 (m, 2H), 7.8 (m, 2H), 8.5 (s,1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-6-bromopyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2005/123733; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 6966-01-4, A common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, 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 2 : 3-amino-6-bromopyrazine-2-carboxylic acid[00211] A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (3 g, 12.93 mmol) and lithium hydroxide (1.548 g, 64.65 mmol) in MeOH (11.74 mL) and H2O (11.74 mL) was heated to 90 0C for 2 hours. The reaction mixture was allowed to cool, neutralised with HCl and diluted with water, and the resultant precipitate collected by filtration (2.2 g, 78% Yield). 1H NMR (400.0 MHz, DMSO) 7.57 (br s, 2H) and 8.39 (s, IH), 13.41 (br s, IH) ppm.

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-damien; DURRANT, Steven; KAY, David; O’DONNELL, Michael; KNEGTEL, Ronald; MACCORMICK, Somhairle; PINDER, Joanne; VIRANI, Anisa; YOUNG, Stephen; BINCH, Hayley; CLEVELAND, Thomas; FANNING, Lev, T.d.; HURLEY, Dennis; JOSHI, Pramod; SHETH, Urvi; SILINA, Alina; WO2010/54398; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6966-01-4,Some common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, 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 3-amino-6-bromopyrazine-2-carboxylate (100 mg, 0.43 mmol) in MeOH (5 mL) was added 2 mL of NaOH aqueous solution (5 N). After being stirred at 50C for 4 h, the mixture was cooled and acidified with 1 M HCl to a pH of 2. The precipitate was collected by filtration and washed with water to afford the product of 3-amino-6- bromopyrazine-2-carboxylic acid (90 mg, yield: 96%). XH-NMR (DMSO-ifc, 400 MHz) delta 8.38 (s, 1H), 7.51-7.56 (m, 2H). MS (M+H)+: 218 / 220.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-6-bromopyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6966-01-4, 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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To the solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (10.0 g 43.1 mmol) in MeOH (70 mL) was added a solution of Li OH (9.0 g, 215 mmol) in water (70 mL). The mixture was stirred at 90 C for 3 hours. The reaction mixture was cooled to rt and acidified to PH = 4-5 with HC1 (2 M). The mixture was filtered to afford 7.4 g of 6 (79 %) as yellow solid. (0170) [0033] LC-MS (M+l): 218.0; 1H MR (400 MHz, DMSO-d6) delta 8.39 (s, 1H), 7.59 (br, 2H).

The chemical industry reduces the impact on the environment during synthesis Methyl 3-amino-6-bromopyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERRIMACK PHARMACEUTICALS, INC.; DRUMMOND, Dary| C.; GENG, Bolin; KIRPOTIN, Dmitri B.; TIPPARAJU, Suresh, K.; KOSHKARYEV, Alexander; ALKAN, Ozan; (142 pag.)WO2017/123588; (2017); 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 6966-01-4 as follows. Product Details of 6966-01-4

To a solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (100 mg, 0.43mmol) in MeOH (5 mL) was added 2 mL of NaOH aqueous solution (5 N). After being stirred at50C for 4 h, the mixture was cooled and acidified with 1 M HC1 to a pH of 2. The precipitate was collected by filtration and washed with water to afford the product of 3-amino-6-bromopyrazine-2-carboxylic acid (90 mg, yield: 96%). ?H-NMR (DMSO-d6, 400 MHz) 8.38 (s, 1H), 7.517.56 (m, 2H). MS (M+H): 218 / 220.

According to the analysis of related databases, 6966-01-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/205593; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, 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 6966-01-4, Recommanded Product: Methyl 3-amino-6-bromopyrazine-2-carboxylate

Example 12.2: Preparation of 3-amino-6-methylpyrazine-2-carboxylic acid methyl ester; 3-Amino-6-bromopyrazine-2-carboxylic acid methyl ester (1.0 g), palladium acetate (0.101 g), and S-Phos (2′-dicyclohexylphosphino-2,6-dimethoxy-l,l’-biphenyl) were placed in a flask, with toluene (15 mL) and water (3 drops). Methyl boronic acid (0.394 g) and potassium phosphate (1.71 g) were added and the reaction mixture was refluxed for 24 hours. After allowing the reaction mixture to cool, the mixture was diluted with aqueous hydrochloric acid (IM) and extracted with ethyl acetate. The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent: diethyl ether) to give 3-amino-6-methylpyrazine-2-carboxylic acid methyl ester as a yellow solid (0.1 14 g).1H NMR (CDCl3): 2.40 (s, 3H), 3.92 (s, 3H), 6.21 (bs, 2H), 8.03 (s, IH) ppm.

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 3-amino-6-bromopyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA LIMITED; WO2008/9908; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6966-01-4, 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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(Step 6-ii) To a solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (1 g, 4.33 mmol) in 10 mL THF was added a solution of LiOH (540 mg, 12.86 mmol) in 20 mL of water. The mixture was stirred at room temperature for 4 hours and acidified with 6M HCl to a pH of 2. The yellow precipitate was collected by filtration and washed with water. After drying in vacuo, the product, 3-amino-6-bromopyrazine-2-carboxylic acid (600 mg, 2.75 mmol, 64% yield), can be used directly in the next reaction without further purification.

The synthetic route of Methyl 3-amino-6-bromopyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/36272; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem