Category: 1458-18-0

Electric Literature of 1458-18-0, The chemical industry reduces the impact on the environment during synthesis 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

Examples 66 and 67[0285] A suspension of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (25.0 gm, 0.113 moles) in 2-propanol (200 mL) was stirred as pyrrolidine (8.84 gm, 0.124 moles) was added. To this mixture was added diisopropyethylamine (16.3gm, 0.126 moles) after which the reaction was heated to reflux. At reflux, a brown solution resulted. After 2 hours at reflux, TLC (silica, 1 : 1 ethyl acetate and hexane) showed all of the starting material had been consumed with the formation of a single product. The reaction was cooled to room temperature which caused the product to crystallize. The solid product was isolated by filtration and was washed with 2- propanol and then with diethyl ether. After drying there was obtained 24.8 gm (85.5%) of the product as a pink solid.

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-5,6-dichloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANUS BIOTHERAPEUTICS, INC.; LIPFORD, Grayson, B.; ZEPP, Charles, M.; WO2012/167046; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1458-18-0,Some common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, molecular formula is C6H5Cl2N3O2, 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.

20.1. Methyl 3-amino-6-chloro-5-(2-methylphenyl)pyrazine-2-carboxylate; Put 5 g (22.5 mmol) of methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, 3.2 g (23.65 mmol) of 2-methylphenyl boronic acid in 45 mL of anhydrous toluene in a screw-top bottle. After dissolution, add 34 mL (67.6 mmol) of a 2N aqueous solution of sodium carbonate and degas the two-phase mixture for 30 min by bubbling with argon. Then add 1.3 g (1.13 mmol) of Pd(PPh3)4 and stir the reaction mixture vigorously at 110 C. for 48 h. After cooling, distribute the solution in 500 mL of EtOAc/brine 1:1 mixture and extract the aqueous phase again with 4¡Á50 mL of EtOAc. Combine the organic phases, dry over Na2SO4and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluting with a cyclohexane/EtOAc gradient from 0 to 20% of EtOAc. After concentration under reduced pressure, we obtain 2 g of methyl 3-amino-6-chloro-5-(2-methylphenyl)pyrazine-2-carboxylate in the form of yellow wax.Yield 50%

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-5,6-dichloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; Sanofi Aventis; US2009/318473; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-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 1458-18-0, Safety of Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

Preparative Example 72. Preparation of Table 1 Compound No. 207; A suspension of 100 (3.6 g, 16 mmol, Aldrich) and sodium hydroxide (1.6 g, 39 mmol) in water (30 ml_) was heated at reflux for 15 min. The solution was filtered, allowed to cool to room temperature, and was acidified with 1 N hydrochloric acid. The precipitated solid 101 (1.2 g, 36% yield) was collected by filtration, air-dried, and dried further under vacuum.

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; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/88920; (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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

A round bottomed flask was charged with methyl 6-amino 2,3-dichloro pyrazine 5-carboxylate (Aldrich, 25 g, 112.6 mmol), 2-S-ethyl piperazine (prepared as per Williams et al J. Med. Chem 1996, 39, 1345, 83% active, 15.7 g, 112.7 mmol), cesium carbonate (100 g, 300 mmol) and 1,4 dioxane (400 mL). The flask was equipped with a reflux condenser and heated to 80 C. After 12 hours the reaction was cooled, diluted with CH2Cl2 (200 mL), and filtered through celite. The filtrate was washed once with water and then concentrated to an oil. The crude product was purified by silica gel column chromatography (3% to 10% MeOH in CH2Cl2) to afford compound A3 (30.8 g, 91%). MS:M+H=300

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US2007/82913; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

1458-18-0, A common compound: 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

S-Amino–chloro-S-methoxy-pyrazine-?-carboxylic acid methyl ester [00442]Methyl 3-amino-5,6-dichloropytauazinoate (1.1 g, 5 mmol) was dissolved in 200 mL of boiling anhydrous methanol containing metallic sodium (115 mg, 5 mmol). The product which separates on cooling, is filtered, washed with water and methanol and dried to give 1.Og (92%) of methyl S-amino-S-methoxy–chloro-pyrazinoate which was recrystallized from acetonitrile. MP. 255-257 C. [00443J 1H NMR (DMSO-rf?, 400MHz): delta 7.61 Qm, 2H, NH2, exchangeable with D2O), 3.97 (s, 3H), 3.80 (s, 3H).

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-5,6-dichloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARDEA BIOSCIENCES INC.; WO2009/89263; (2009); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

1458-18-0, A common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, molecular formula is C6H5Cl2N3O2, 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.

General procedure: To a solution of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (1.0 eq.) in 2-propanol (5 mL/mmol), an appropriate primary or secondary amine(3-6 eq.) was added, and the reaction mixture wasrefluxed for 2 h.10) The solution was cooled to roomtemperature, concentrated under reduced pressure, andthe residue was purified by silica-gel column chromatography(Wako gel C-200, 30-40% ethyl acetate/n-hexane) to afford the series 1 intermediate (yield:32-95%). The regioselectivity of the nucleophilicsubstitution at the 5-position of the pyrazine ring wasconfirmed by an X-ray structural analysis (Fig. S1).

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Murai, Masatoshi; Habu, Sayako; Murakami, Sonomi; Ito, Takeshi; Miyoshi, Hideto; Bioscience, Biotechnology and Biochemistry; vol. 79; 7; (2015); p. 1061 – 1066;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, molecular formula is C6H5Cl2N3O2, 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. 1458-18-0

A. 2-Amino-5,6-dichloro-3-(hydroxymethyl)pyrazine To 70 ml of dry tetrahydrofuran there was added 2-amino-5,6-dichloro-3-(methoxycarbonyl)pyrazine (8.8 g; 0.04M), potassium borohydride (2.7 g; 0.05M), and lithium chloride (2.1 g; 0.05M), and the mixture was stirred at room temperature overnight (17 hours). The reaction mixture was then diluted with about 200 ml of water and chilled, after which the product crystallized, was filtered and dried (5.3 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1458-18-0, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US4507299; (1985); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

1458-18-0, Name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, 1458-18-0, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

The mixture of methyl 3-amino-5, 6-dichloropyrazine-2-carboxylate (4.4 g, 19.91 nMol) , 2- (4-fluorophenyl) -4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane (3.07 g, 21.9 nMol) in dioxane (50 mL) and water (5 mL ) was added Na 2CO 3 (4.22 g, 39.82 nMol) and dppfPdCl 2 (2.84 g, 3.98 nMol) . Then the mixture was stirred at 100 for 1 h under N 2 atmosphere. Then the mixture was concentrated and residue was poured to water (100 mL) and then extracted with EA (100 mL x 3) . The organic solution was then concentrated to afford the crude product (5.5 g, 98%yield) as a yellow solid which was used for next step without further purification. MS m/z (ESI) [M+H] + = 282.2.

Statistics shows that Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate is playing an increasingly important role. we look forward to future research findings about 1458-18-0.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; QI, Changhe; TSUI, Honchung; ZENG, Qingbei; YANG, Zhenfan; ZHANG, Xiaolin; (399 pag.)WO2020/35052; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

1458-18-0, 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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (1.0 eq.) in 2-propanol (5 mL/mmol), an appropriate primary or secondary amine(3-6 eq.) was added, and the reaction mixture wasrefluxed for 2 h.10) The solution was cooled to roomtemperature, concentrated under reduced pressure, andthe residue was purified by silica-gel column chromatography(Wako gel C-200, 30-40% ethyl acetate/n-hexane) to afford the series 1 intermediate (yield:32-95%). The regioselectivity of the nucleophilicsubstitution at the 5-position of the pyrazine ring wasconfirmed by an X-ray structural analysis (Fig. S1).

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:
Article; Murai, Masatoshi; Habu, Sayako; Murakami, Sonomi; Ito, Takeshi; Miyoshi, Hideto; Bioscience, Biotechnology and Biochemistry; vol. 79; 7; (2015); p. 1061 – 1066;,
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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., 1458-18-0

Under an argon atmosphere,Isoamyl nitrite (26.6 mL, 200 mmol) was added to a THF solution of methyl 3-amino-5,6-dichloropyrazine-2-carboxylate (4.44 g, 20.0 mmol) in THF (30 mL). The reaction mixture was stirred at 80 C. for 17 hours. After standing to cool, the low boiling point compound was distilled off to obtain a crude product. This crude product was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 100/0 to 90/10) to obtain methyl 5,6-dichloropyrazine-2-carboxylate (2.29 g, 55% ) As a white solid.

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; TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH INSTITUTE; AIHARA, HIDENORI; SHONO, TOMOHIRO; (23 pag.)JP2015/140319; (2015); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem