Month: September 2021

Reference of 27398-39-6, The chemical industry reduces the impact on the environment during synthesis 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life.

[00156] Acid chloride obtained from Step 1, was taken up in dichioromethane (20 mL) and a solution of 2 (11.5 mmols, 1.9 g, 0.9 eq) and triethyl amine (38.2 mmols, 3.86 g, 3.0 eq) in dichloromethane (10 mL) was added dropwise at 0 °C. The reaction was stirred at 25 °C for 30 mm. The reaction progress was monitored by TLC. It was then diluted with dichloromethane, and washed successively with saturation solution ammonium chloride, saturation solution sodium bicarbonate and brine. The crude product was purified by silica gel chromatography (Petroleum ether/ethyl acetate, 4/1) to give the desired product 14 (2.00 g, 6.53 mmols, 5 1.3percent) as a white solid.: [00161] Compound 30 was similarly prepared as the synthesis of Intermediate 14, while in Step 2, pyridine was used as the base and solvent. Yield: 44.2percent

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-Chloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALPHARMAGEN, LLC; PUTMAN, David, G.; DASSE, Olivier; HOGENKAMP, Derk; (154 pag.)WO2016/144792; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 69214-33-1, 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 69214-33-1 as follows.

A mixture of 8-chloroimidazo[1,2-a]pyrazine(500 mg, 3.25 mmol) and (S)-tert-butyl pyrrolidin-3-yl carbamate (1.0 g, 5.38 mmol) in diethylisopropyl amine (3 mL) was heated to 120 C. for 3 h. After cooling to room temperature, the mixture was diluted with 10% MeOH in EtOAc and washed with saturated aqueous solutions of KH2PO4 andNaHCO3, followed by brine. The organic layer was concentrated in vacuo and the residue purified by flash chromatography (Si02, 2 to 5% MeOH in CH2C12 as eluent) to give thedesired compound as a foam (985 mg, quantitative, which was used directly for the next step). MS: (ES) m/z 304.1(M+H+).

According to the analysis of related databases, 69214-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 109-08-0, A common heterocyclic compound, 109-08-0, name is 2-Methylpyrazine, molecular formula is C5H6N2, 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.

In the glove box, Mn(CO)5Br (0.005mmol), [(E)-2-(2-(1-(2-pyridine)ethylidene)-indenyl)pyridine] (0.006 mmol),After adding 1.0 mL of toluene and stirring for two hours, 2-methylpyrazine 1a (2 mmol) was added.Benzyl alcohol 2e (1 mmol), after reacting at 135 ° C for 48 hours, the reaction was stopped, and the solvent was evaporated to dryness.Column chromatography ethyl acetate / petroleum ether (1:10),Trans-disubstituted olefin derivative 3e. The product was a white solid with a yield of 83percent.

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; Qingdao University of Science and Technology; Zhang Chunyan; (19 pag.)CN108250153; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6164-79-0, name is Methyl 2-pyrazinecarboxylate, 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 6164-79-0, Formula: C6H6N2O2

To a mixture of NaH (60% in mineral oil, 0.68 g, 28.2 mmol),methyl pyrazine-2-carboxylate (3 g, 21.7 mmol) and dry DMF(30 mL), methyl acetate (2.09 g, 28.2 mmol) was added dropwiseunder N2 atmosphere. After being stirred at rt for 5 h, the reactionmixture was concentrated in vacuo, and the residue treated withsaturated aqueous NaHCO3 solution followed by extraction withEtOAc. The combined organic phase were dried with MgSO4,filtered, and concentrated in vacuo. Column chromatographicpurification (n-hexane/EtOAc = 8:1) yielded 5a as white solid(1.95 g, 50%). 1H NMR (CDCl3, 400 MHz) d keto form: 9.28 (d, 1H,J = 1.5 Hz), 8.80 (d, 1H, J = 2.4 Hz), 8.66 (overlapped, 1H), 4.18 (s,2H), 3.74 (s, 3H); enol form: 12.30 (s, 1H), 9.15 (d, 1H, J = 1.5 Hz),8.66 (overlapped, 1H), 8.60 (dd, 1H, J = 2.3, 1.5 Hz), 6.34 (s, 1H),3.85 (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 2-pyrazinecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lee, Young Hun; Lee, Jung Min; Kim, Sang Geon; Lee, Yong Sup; Bioorganic and Medicinal Chemistry; vol. 24; 12; (2016); p. 2843 – 2851;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89123-58-0, name is 5-Bromopyrazine-2,3-diamine, 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 89123-58-0, name: 5-Bromopyrazine-2,3-diamine

(b) Add Compound II (7.8 g, 41.3 mmol, 1 eq) to a 250 mL vial.80 mL of DMF (ie, N,N-dimethylformamide) was added under constant stirring to dissolve Compound II.Triethyl orthoformate (7.34 g, 49.5 mmol, 1.2 eq) was added dropwiseAnd 20ml formic acid (about 1 drop / sec),Heating under reflux conditions for 24 h under nitrogen protection (at this time, TLC detection is basically free of raw materials);Unscrew the solvent and dissolve in methanol.Purification by silica gel column chromatography gave 5 g of compound III.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromopyrazine-2,3-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Suzhou Derivative Biological Technology Co., Ltd.; Liu Ke; (6 pag.)CN108395436; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 23611-75-8, name is Methyl 6-chloropyrazine-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. Quality Control of Methyl 6-chloropyrazine-2-carboxylate

Methyl 6-(chloropyrazine)-2-carboxylate (13) (2g, 0.0115mmol) was dissolved in 80mL of 87 DMSO. 88 Sodium azide (3g, 0.0463mmol) and 39 triphenylphosphene (4.6g, 0.1738mmol) were added and refluxed at 120C for 4h. 20mL of 1N 89 HCl was added and the reaction was continued at 120C for 2h. The mixture was cooled and neutralized by aqueous NaHCO3 solution and 131 product was extracted in ethyl acetate, dried with Na2SO4 which was then concentrated and dried with n-pentane to get 1.4g of compound 14 as yellow solid (yield 82.4%). 1H NMR (400MHz, DMSO-d6) delta 8.28-8.27 (m, 1H), 8.07 (s, 1H), 6.90 (s, 2H), 3.84 (s, 3H). C6H7N3O2 [M]: 153.14; MS (ESI) m/z: [M+H]+: 154.05

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

Reference:
Article; Trivedi, Prakruti; Adhikari, Nilanjan; Amin, Sk. Abdul; Jha, Tarun; Ghosh, Balaram; European Journal of Pharmaceutical Sciences; vol. 124; (2018); p. 165 – 181;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 221136-66-9, 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. 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, This compound has unique chemical properties. The synthetic route is as follows.

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.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/146553; (2007); 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. 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 13301-04-7

To a solution of methyl 2,5-dibromo pyrazine carboxylate (40g, 135mmol) in toluene (300ml) were dropwise added K2CO3 (28g, 202mmol) and N-ethyl-N- cyclohexylamine (35g, 270mmol). The reaction mixture was refluxed at 120C for 3 with stirring, and then cooled to room temperature. After extraction with ethyl acetate, the organic layer thus formed was washed with 2N HCI and further with water. Then, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in a vacuum to afford the title compound (46g, 99%). 1H NMR (400MHz, CDCI3) 8.15 (s, 1 H), 3.92 (s, 3H), 3.50 (, 3H), 1.81 (m, 4H), 1.66 (m, 2H), 1.57 (m, 2H), 1.28 (m 2H), 1.12 (t, 3H).

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; DONG-A ST CO.,LTD; PARK, Jang Hyun; SONG, Seung Hyun; CHUNG, Han Kook; KIM, Heung Jae; LEE, Ji Hye; JANG, Byeong Jun; KIM, Eun Jung; JUNG, Hae Hum; RYU, Chae Lim; HWANG, Jae-Sung; LEE, Hyung Ki; KANG, Kyung Koo; KIM, Soon Hoe; WO2014/157994; (2014); 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. 19847-12-2, name is Pyrazinecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Pyrazinecarbonitrile

2-Cyanopyrazine (1.0g, 9.5mmol) was dissolved in dry methanol (50mL) with stirring at room temperature. Metallic sodium (0.12g, 5.2mmol) was added and the mixture refluxed for 2h. The clear yellow solution of the in situ iminoester was brought to neutral pH with glacial acetic acid resulting in a clear orange solution. 2-(Hydoxyimino)-propanehydrazone [14,15] (1.1g, 9.3mmol) was added and the resulting solution refluxed for 1h, and stirred at room temperature overnight. The white solid formed was separated by suction filtration and washed with methanol and diethylether (Yield: 1.85g, 90%). 1H NMR (300MHz, DMSO-d6, 298K) delta (ppm) 11.72 (s, 1H, N-OH), 10.03 (s, 1H, NH), 9.27 (d, 1H, CH(pyz)), 8.70 (d, 1H, CH(pyz)), 8.64 (dd, 1H, CH(pyz)), 6.99 (s, 2H, NH2), 1.95 (s, 3H, CH3). 13C{1H} NMR (75.4MHz, DMSO-d6, 298K) delta (ppm) 160.52 (C=O), 150.66, 146.14 (C=N), 146.04 (C(pyz)), 145.01, 142.86, 142.72 (CH(pyz)), 10.20 (CH3). Selected IR data (cm-1): 3247 br (nu N-H), 1650 s (nu C=O), 1621 s, (nu C=N), 1045 s (nu N-Ooxime). M. pt. 240-242C.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 19847-12-2.

Reference:
Article; Drover, Marcus W.; Tandon, Santokh S.; Anwar, Muhammad U.; Shuvaev, Konstantin V.; Dawe, Louise N.; Collins, Julie L.; Thompson, Laurence K.; Polyhedron; vol. 68; (2014); p. 94 – 102;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 19847-12-2, 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. 19847-12-2, name is Pyrazinecarbonitrile belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(1) preparing a format reagent,Add magnesium, anhydrous polarity to a nitrogen-protected pressure vesselSolvent tetrahydrofuran and elemental iodine, then add methyl chloride to the pressure vessel and stir.After the pressure vessel is heated to 60 C and stirring is continued for 2 hours, a format reagent is prepared;Metal magnesium is newly formed magnesium, and the molar ratio of magnesium metal to chloromethane acid is 1:1.1;The content of elemental iodine is 0.21% × metal magnesium weight; the reaction equation is as follows:(2)Addition reaction, adding 2-cyanopyrazine and tetrahydrofuran to the reactor and heating the reactor to50 C, then add catalysisThe cuprous chloride and the reagents of the above format are then refluxed and condensed.After the end, the remaining part of the reactor is an intermediate product, wherein the addition reaction time is 14h;The molar ratio of 2-cyanopyrazine to the format reagent S1 is1:1.05; the content of cuprous chloride is 2.1% metal magnesium weight;(3)Hydrolyzing, adding water to the remaining intermediate product of the above reactor,The pH of the solution in the reactor was adjusted to 1 with dilute sulfuric acid, and then stirred for 12 hours.Adjusting the pH of the solution in the reactor to neutral with a saturated aqueous solution of sodium carbonate;Finally extracted with toluene three times;(4)After the treatment, the toluene extract is desolvated, and the solid after desolvation is dissolved by heating with ethanol.Add activated carbon, continue heating and reflux for 10 min, and filter.The filtrate was cooled to 5 C to obtain a white solid P1; then the white solid P1 was recrystallized from ethanol.Produced a white solid P2,Drying gives 2-acetylpyrazine;The purity of 2-acetylpyrazine was 98.4%, and the yield of 2-acetylpyrazine was 69%.The reagent polar solvents, elemental iodine, 2-cyanopyrazine, tetrahydrofuran toluene and ethanol were all analytically pure.

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, Pyrazinecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Henan Weiyuan Biological Technology Co., Ltd.; Xuan Bingwu; Xing Xiaodong; Xuan Fuxing; (8 pag.)CN109796416; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem