Tag: M.W=100-200

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

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

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

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

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

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 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

Related Products of 77168-85-5, 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. 77168-85-5, name is Methyl 5-chloro-6-methylpyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: methyl 5-(5-fluoro-2-methoxypyridin-4-yl)-6-methylpyrazine-2-carboxylate To a nitrogen-purged solution of methyl 5-chloro-6-methylpyrazine-2-carboxylate (15 g, 80 mmol), (5-fluoro-2-methoxypyridin-4-yl)boronic acid (16.49 g, 96 mmol), Pd (dppf) Cl2 dichloromethane adduct (1.2 g,1.469 mmol) and Pd(dppf)C12 (4.6 g, 6.29 mmol) in THF (199 ml) and water (40.8 ml) was addedpotassium phosphate tribasic (51.2 g, 241 mmol) under a nitrogen atmosphere. A reflux condenserwas attached and the mixture was vigorously refluxed with a 100 °C oil bath with stirring. After 105mm, the reaction was cooled to rt and partitioned between EtOAc (200 mL) and water (200 mL).The layers were separated and the aqueous layer was extracted with ethyl acetate (150 mL). Theorganic layers were combined, filtered through C eliteTM, washed with brine, dried over anhydrousMg504, filtered and evaporated to afford a crude residue. The resulting residue was purified via column chromatography on silica gel (ISCO RediSep Gold 330g silica gel column, gradient elution with 0percent to 50percent EtOAc in hexanes) to give the title compound.

The chemical industry reduces the impact on the environment during synthesis Methyl 5-chloro-6-methylpyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHEN, Helen; COLLETTI, Steven, L.; DEMONG, Duane; GUO, Yan; MILLER, Michael; NAIR, Anilkumar; PLUMMER, Christopher, W.; XIAO, Dong; YANG, De-Yi; (289 pag.)WO2016/22742; (2016); 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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Chloropyrazine-2-carboxylic acid

N,N-dimethylformamide (1 drop) is added to a flask charged with a stir bar, 5-chloro- pyrazine-2-carboxylic acid (13.17 g), thionyl chloride (25 mL), and toluene (200 mL) at room temperature. The mixture is stirred at 60 00 overnight. After cooling to room temperature, the mixture is concentrated, and the remainder is freed from volatile residues by three times repeated evaporation with toluene.

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 36070-80-1.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; WAGNER, Holger; (77 pag.)WO2018/138028; (2018); 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. 56423-63-3, name is 2-Bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

General procedure: Method S Parallel preparation of Examples 39-40: To a set of vials containing the requisite aryl bromide (0.12 mmol) was added bis[(tetrabutylammonium iodide)copper(I) iodide] (3.9 mg, 0.0034 mmol), 1,10 phenanthroline (2.5 mg, 0.014 mmol) followed by Cs2C03 (68 mg, 0.21 mmol). The vials were capped and transferred into a glove box under an atmosphere of nitrogen. To each vial was added a solution of H2 (30 mg, 0.069 mmol) in dioxane (1.0 mL). The vials were capped and the mixtures were heated at 100 C with stirring overnight. After that time, the mixtures were allowed to cool to RT. To each vial was added water (2 mL) and DCM (2 mL). The mixtures were transferred to a set of fritted barrel filters. The organic layer from each mixture was drained into a clean vial. Additional DCM (1 mL) was added to each aqueous layer and the organic layer was again drained and combined with the previous organic extract. The solvent from the combined organic layers was removed in vacuo. The crude residues were dissolved in DMSO (1 mL) and filtered. The crude products were purified by mass triggered reverse phase HPLC using the following conditions: [column: Waters XBridge CI 8, 5muiotaeta, 19×100 mm; solvent gradient: 19-21% initial to 49-51% final MeCN (0.1% NH4OH) in water (0.1% NH4OH) 25 mL/min; 8 min run time] to afford Examples 39-40.

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 56423-63-3.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; CUMMING, Jared, N.; LIU, Hong; SCOTT, Jack, D.; (0 pag.)WO2016/85780; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem