Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, 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 221136-66-9, Computed Properties of C9H11BrN2O3

Example 8 r3-(2,2-Difluoro-2-phenyl-ethylamino)-6-methyl-2-oxo-2H-pyrazin-1-vn- acetic acid ethyl ester(3-Bromo-6-methyl-2-oxo-2H-pyrazin-1 -yl)-acetic acid ethyl ester was reacted with 2,2-difluoro-2-phenyl-ethylamine in the presence of a base, at elevated temperature, to yield the title compound as shown in the Scheme above. Table 5 below lists the reagent amounts, base and temperature combinations applied to this reaction, as well as yield.

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; JANSSEN PHARMACEUTICA, N.V.; WO2007/146553; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, 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. Quality Control of 5-Chloropyrazine-2-carbonitrile

Step 1: 5-(4-fluoro-1H-pyrazol-1-yl)pyrazine-2-carbonitrile To a solution of 5-chloropyrazine-2-carbonitrile (280 mg, 2.0 mmol) in DMF was added 4-fluoro-1H-pyrazole (170 mg, 2.0 mmol), and potassium acetate (395 mg, 4.0 mmol). The mixture was stirred at the 100 C. for 4 hours. The reaction mixture was cooled to 20 C., poured into brine (25 mL), and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and purified by column chromatography (hexane:ethyl acetate=5:1) to give 5-(4-fluoro-1H-pyrazol-1-yl)pyrazin-2-carbonitrile (310 mg, Yield 82%). The structure was confirmed by LC-MS.

The synthetic route of 5-Chloropyrazine-2-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Kim, Joseph L.; Kevin, Douglas J.; Brubaker, Jason D.; (57 pag.)US2017/267661; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6164-79-0,Some common heterocyclic compound, 6164-79-0, name is Methyl 2-pyrazinecarboxylate, 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.

Step 2; Lithium aluminum hydride (40.0 mg, 1.06 mmol) was suspended in tetrahydrofuran (1.0 mL). To this, a solution of methyl 2-pyrazinecarboxylate (66.0 mg, 0.478 mmol) in tetrahydrofuran (0.5 mL) was added dropwise under a nitrogen atmosphere at 0 C. and the mixture was stirred at the same temperature for 15 minutes. Then, water (40 muL), a 15% aqueous sodium hydroxide solution (40 muL) and water (120 muL) were successively added to the reaction mixture and the mixture was stirred at room temperature for 1 hour. The mixture was filtered through Celite and the mother liquid was concentrated. The residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give 2-pyrazinemethanol (Compound CD) (19.0 yield: 36%).1H-NMR (270 MHz, CDCl3, delta): 3.11 (brd, J=5.6 Hz, 1H), 4.85 (d, J=5.6 Hz, 1H), 8.52-8.55 (m, 2H), 8.64 (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 2-pyrazinecarboxylate, its application will become more common.

Reference:
Patent; Amishiro, Nobuyoshi; Fukuda, Yuichi; Kinpara, Keisuke; Mie, Motoya; Tagaya, Hisashi; Takahashi, Takeshi; US2011/237584; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 56423-63-3, name is 2-Bromopyrazine, 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 56423-63-3, Application In Synthesis of 2-Bromopyrazine

2-Bromopyrazine (163 mg, 1.02 mmol), bis(triphenylphosphine)palladium(II) chloride (18 mg, 0.03 mmol) was dissolved in DMF (2 mL) under Ar atm. The hexamethylditin (0.214 mL, 1.02 mmol) was added and the reaction mixture was heated to 130 C. for 30 minutes with MW. 2-amino-5-(3-bromo-4-fluorophenyl)-3-methyl-5-[4-(pentafluoro-lambda6-sulfanyl)phenyl]-3,5-dihydro-4H-imidazol-4-one (250 mg, 0.51 mmol), cesium fluoride (0.076 mL, 2.05 mmol) and additional 2 mol % of bis(triphenylphosphine)palladium(II) chloride was added, and the reaction mixture was heated to 130 C. for 2 h. The reaction mixture was filtrated through a short silica column using EtOAc as eluent. The solution was concentrated in vacuo. The residue was dissolved in DMSO (2 mL) and purified by preparative HPLC to give the title compound (22 mg, 8%): 1H NMR (400 MHz, CDCl3) delta ppm 8.97-8.99 (m, 1H); 8.59-8.61 (m, 1H); 8.47 (d, J=2.5 Hz, 1H); 8.04 (dd, J=7.1, 2.5 Hz, 1H); 7.62-7.67 (m, 2H); 7.54-7.59 (m, 2H); 7.44-7.49 (m, 1H); 7.12 (dd, J=10.48, 8.72 Hz, 1H); 3.08 (s, 3H); 1.99 (s, 2H); MS (ES) m/z 488.0 [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; Astex Therapeutics Limited; AstraZeneca AB; US2008/287460; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1215852-11-1, A common heterocyclic compound, 1215852-11-1, name is 7-tert-Butyl 3-ethyl 5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-3,7(8H)-dicarboxylate, molecular formula is C13H20N4O4, 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 flask was charged with 7-(t-butyl) 3-ethyl 5,6-dihydro-[l,2,4]triazolo[4,3-a]pyrazine- 3,7(8H)-dicarboxylate (3.00 g, 10.1 mmol, 1.00 equiv), Li OH (1.21 g, 30.3 mmol, 3.00 equiv), EtOH (20 mL) and water (2 mL). The resulting solution was stirred for 2 h at room temperature and concentrated under reduced pressure to provide 2.70 g (crude) of 7-(t-butoxycarbonyl)- 5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyrazine-3-carboxylic acid. LCMS (ESI, m/z): 269 [M+H]+

The synthetic route of 1215852-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; WEBER, Olivia D.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; JONES, Todd K.; (275 pag.)WO2019/46318; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4774-14-5, The chemical industry reduces the impact on the environment during synthesis 4774-14-5, name is 2,6-Dichloropyrazine, I believe this compound will play a more active role in future production and life.

Svnthesis 2-1-A 6-Chloropyrazin-2-amine 2,6-Dichloropyrazine (2.89 g, 19.4 mmol) was stirred in aqueous ammonia (28%, 10 mL) and heated to 100C overnight in a sealed tube. The reaction mixture was cooled and the resultant precipitate was filtered. Trituration with water and then ether gave the title compound as a white solid (2.28 g, 17.6 mmol, 91%). 1H NMR (d6-DMSO, 400 MHz) delta 7.80 (d, 1 H1 J = 0.4 Hz), 7.70 (d, 1 H, J = 0.4 Hz), 6.9 (br s, 2H). LC-MS (2) rt 1.05 min; m/z (ESI+) 130/132.

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, 2,6-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/103966; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 356783-26-1, The chemical industry reduces the impact on the environment during synthesis 356783-26-1, name is Methyl 3,6-difluoropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

(b) In 4 mL of methanol was dissolved 0.2 g of methyl 3,6-difluoro-2-pyrazinecarboxylate. Then, a 28% methanol solution of sodium methoxide was added at -25 C., and the mixture thus obtained was stirred at 0 C. for 10 minutes. The reaction mixture was poured into a mixture of 30 mL of ethyl acetate and 30 mL of water, and the organic layer was separated. The organic layer thus obtained was washed successively with 15 ml of water and 15 mL of saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel chromatography [eluent: n-hexane:ethyl acetate=5:1] to obtain 0.09 g of methyl 6-fluoro-3-methoxy-2-pyrazinecarboxylate as a colorless solid product.

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

Reference:
Patent; Toyama Chemical Co., Ltd.; US2003/130213; (2003); 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

Reference of 54013-06-8,Some common heterocyclic compound, 54013-06-8, name is Ethyl 5-aminopyrazine-2-carboxylate, molecular formula is C7H9N3O2, 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: Ethyl 5-amino-6-bromopyrazine-2-carboxylate: To a solution of ethyl 5-aminopyrazine-2-carboxylate (880 mg, 5.26 mmol) in acetonitrile (20 mL) at RT was added NBS (984 mg, 5.53 mmol), the resultant solution was stirred at RT for 1 hour. The reaction mixture was diluted with EtOAc, washed with sat NaHCO3, brine and water, dried, filtered, and concentrated to afford the crude product, which was purified by ISCO 24 g silica gel column, 0 to 50% EtOAc in Heptane, 30 min). 1.01 g, 78% yield. LC-MS (m/z): 247.9 (MH+), 0.51 min.

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

Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1208082-91-0, 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. 1208082-91-0, name is 6,8-Dibromo-2-methylimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 1-05 (0.62 g, 2.13 mmol) was dissolved inCHC1 (4 mE) and N-bromosuccinimide (455 mg, 2.56mmol) was added. The reaction mixture was heated under microwave irradiation at 120 C. for 1 h. On cooling, the mixture was adsorbed in silica and purified by l3iotage column chromatography (DCMJMeOH from 100% to 95:5) to give intermediate 1-06 (720 mg, Y: 91%) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 6,8-Dibromo-2-methylimidazo[1,2-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); Serrano Marugan, Manuel; Pastor Fernandez, Joaquin; Martinez Gonzalez, Sonia; Ortega Molina, Ana; Bischoff, James R.; Oyarzabal Santamarina, Julen; (220 pag.)US9993554; (2018); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem