Tag: M.W=100-200

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. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine

General procedure: A mixture of chloro compound (50 mg) and amine derivative (2 equiv.) in PEG 400 (2 mL) wasstirred at 120 C for 5 min. After completion the reaction was then cooled to room temperature. DCM and water were added and the phases were separated. The aqueous phase was extracted withDCM and the organic phase was dried and filtered. The removal of solvent gave the product as solid.

According to the analysis of related databases, 68774-77-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Campos, Joana F.; Loubidi, Mohammed; Scherrmann, Marie-Christine; Berteina-Raboin, Sabine; Molecules; vol. 23; 3; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19745-07-4, name is 2,5-Dichloropyrazine, 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 19745-07-4, Safety of 2,5-Dichloropyrazine

Intermediate C-5 2-chloro-3-((5-chloropyrazin-2-yl)thio)aniline A mixture of 3-amino-2-chlorobenzenethiol (724 mg, 3.69 mmol), 2,5- dichloropyrazine (500 mg, 3.36 mmol), and potassium carbonate (1.39 g, 10.07 mmol) in DMF/MeCN (1/1, 20 mL) was stirred for 4 h at 85 °C. After cooling to RT, the reaction mixture was filtrered through a pad of Celite followed by MeCN (10 mL) wash. The combined filtrates were concentrated under reduced pressure and the resulting residue was purified by silica chromatography (0 to 20percent gradient of EtO Ac/heptane) to give 2-chloro-3-((5-chloropyrazin-2- yl)thio)aniline (285 mg, 1.037 mmol). MS m/z. 272.1 (M+H)+.

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

Reference:
Patent; NOVARTIS AG; CHEN, Zhuoliang; FORTANET, Jorge Farcia; JOUK, Andriana; KARKI, Rajesh; LAMARCHE, Matthew J.; LIU, Gang; PALERMO, Mark G.; PEREZ, Lawrence Blas; SARVER, Patrick James; SHULTZ, Michael David; SENDZIK, Martin; TOURE, Bakary-Barry; YU, Bing; (173 pag.)WO2016/203406; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

98-97-5, name is Pyrazine-2-carboxylic acid, 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. Formula: C5H4N2O2

Step A. Preparation o f Pyrazine-2-carbonyl chloride. A 500 ml three neck round bottomed flask equipped with a stir bar, thermocouple, heating mantle with digital temperature controller, condenser and nitrogen inlet/outlet was charged with 15 g (0.12 mol) of pyrazine carboxylic acid, 225 mL of toluene (Kf < 0.02wt%) and 26.4 ml (43 g, 0.36 mol) of thionyl chloride. The thin slurry was heated to 75 C and stirred overnight (10-16 hr). After cooling the reaction mixture to room temperature the solvent and excess thionyl chloride were removed in vacuo as follows: Reaction mixture was stripped under full vacuum at 60 C (bath temperature) to approximately 1/3 its original volume and then (175 ml) of fresh toluene was added. Concentration was continued, again stripping to 1/3 original volume followed by re-dilution with 225 ml of fresh toluene to provide the pyrazine acid chloride in a toluene solution. The synthetic route of 98-97-5 has been constantly updated, and we look forward to future research findings. Reference:
Patent; CEPHALON, INC.; ROEMMELE, Renee Caroline; WO2011/87822; (2011); 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. 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H3ClN2O2

To a suspension of sodium hydride (278 mg, 6.95 mmol, 60percent in oil) in DMF (10 mL) was added 1H-pyrazole (279 mg, 4.11 mmol) at RT and the resulting mixture was stirred at room temperature for 30 mins. 3-Chloropyrazine-2-carboxylic acid (500 mg, 3.16 mmol) wasadded and the mixture heated to 60 °C for 2 h. After cooled to RT, water (20 mL) was added and the mixture extracted with 4.7percent MeOH in DCM (20 mL x 3). The combined organic layers were washed with brine, dried over Na2504, filtered, and concentrated in vacuo to give the title compound. LRMS m/z (M+H) 191.0 found, 191.0 required.

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 27398-39-6.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (97 pag.)WO2016/100157; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 109838-85-9,Some common heterocyclic compound, 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, molecular formula is C9H16N2O2, 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.

Example 1; (2S)-2- (fert-butoxycarbonyl) aminol-3-cLrcloheptylpropanoic acid building block; a) Methyl (2S)-2-amino-3-cycloheptylpropanoate; To a stirred solution of R-2,5-dihydro-3, 6-dimethoxy-2-isopropyl pyrazine (5 g, 27 mmol) in THF (80 mL) at-78 °C was added dropwise 2.5 M n-butyllithium in hexanes over 40 min, maintaining the temperature of the reaction mixture below-70 °C. To the reaction mixture was added dropwise a solution of iodomethylcycloheptane (Webb et al, J. Med. Chem. , 42,8 (1999), 1415-1421. ) (6.8 g, 28. 5 mmol) in THF (12 mL) over 50 min, maintaining the temperature of the reaction mixture below-70 °C. The reaction mixture was then stirred at 0 °C for another 75 min, acetic acid was added (2.45 mL) and stirring was continued for another 20 min. The reaction mixture was then diluted with ethyl acetate (200 mLI), washed with brine (2 x 50 mLI), dried (MgS04), filtered and concentrated in vacuo. Column chromatography of the residue using stepwise gradient elution (ethyl acetate in hexane 0-5percent) gave the pyrazine derivative as an oil (5.4 g, 68percent). A mixture of the pyrazine derivative (5.4 g, 18.5 mmol) in acetonitrile (55 mL), water (45 mL) and 1 M aqueous hydrochloric acid (45 mL) was stirred at room temperature for 2 h, then concentrated in vacuo to approximately half the volume. Aqueous NaHCO3 (1 M) was added until just alkaline, then the reaction was extracted with dichloromethane (3 x 50 mL). The extracts were dried (MgSO4), filtered and concentrated in vacuo onto silica. Column chromatography of the residue using stepwise gradient elution (ethyl acetate in hexane and triethylamine (0.5percent) 20-100percent) gave pure fractions of (8) which were concentrated in vacuo to a syrup (2.14 g, 58percent). Additional material could be obtained by repeated chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, its application will become more common.

Reference:
Patent; MEDIVIR UK LTD; PEPTIMMUNE, INC; WO2005/82876; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 186534-02-1, The chemical industry reduces the impact on the environment during synthesis 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, I believe this compound will play a more active role in future production and life.

General procedure: To a stirred solution of 4-1 (0.25 mmol) in CH3OH (1.5 mL) andTHF (1.5 mL) was added compounds 5a-q (0.28 mmol) at room temperature.Keep stirring for 2-9 h to give intermediate 6a-q which wasdirectly cooled to 0 C without any treatment. Then the mixture wasadded to NaBH4 (1.25 mmol), keeping stirring for 2 h. The reaction wasquenched with 10% HCl aqueous and directly evaporated to dryness.The residue was basified with saturated NaHCO3 solution and extractedwith DCM (3 × 10 mL). Subsequently, the combined organic layerswere washed with brine (20 mL), dried over Na2SO4, filtered, concentratedand purified via column chromatograph (eluting solvent:pentane/ethyl acetate=10/1 to 4/1) to afford the desired products 7aq.Meanwhile, product 7r was obtained from compound 4-2 andcompound 5i by the same synthesis method. The yield is 47-76%.

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, 3,5,6-Trimethylpyrazine-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cao, Zhongcheng; Deng, Yong; Liu, Zhuoling; Song, Qing; Tan, Zhenghuai; Yang, Ziyi; Yu, Guangjun; Bioorganic and medicinal chemistry; (2020);,
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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H7N3O2

A solution of methyl 3-aminopyrazine-2-carboxylate (3.0 g, 19.6 mmol) and NBS(3.5 g, 23.5 mol) in MeCN (70 mL) was stirred at 70C for 5 h. Then the mixture was concentrated and extracted with EtOAc. The organic layer was washed with Na2503 (a.q.) and brine, dried over Na2504 and concentrated in vacuo. The crude product of methyl 3-amino-6-bromopyrazine-2-carboxylate (3.0 g, yield: 92%) was used for next step without further purification. ?H-NMR(CDC13, 400 MHz) 8.18 (s, 1H), 6.546.93 (m, 2H), 3.86 (s, 3H). MS (M+H): 232 / 234.

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; 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

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. 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C5HCl2N3

A nilxture of 3,5-dichloropyrazine-2-carbonitrile (150 mg, 0.87 mmol), 1- methyl-4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrazole (180 mg 0.87 mmol, 1.0 equiv), [1,1 ?-bis(diphenylphosphino)ferroceneldichloropalladium(II) (0.04 mmol, 5 mol%) in degassed THF (1.7 mL) and aq. solution of sodium carbonate (2 M, 850 jiL) was stirred for 4h under nitrogen at 100C. Once complete, the reaction was diluted with EtOAc and water. The organic phase was separated and the aqueous layer was extracted twice with EtOAc, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give product: ESI-MS (mlz): 220.1

The synthetic route of 313339-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford; ANTCZAK, Monika; READY, Joseph; ZHANG, Youngyou; (332 pag.)WO2018/218251; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 33332-29-5, name is 2-Amino-5-chloropyrazine, molecular formula is C4H4ClN3, 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. Recommanded Product: 2-Amino-5-chloropyrazine

1 , 1 -Dimethylethyl (5-chloro-2-pyrazinyl)carbamateTo a 500 mL flask was added THF (83 mL), 5-chloropyrazin-2-amine (10 g, 77 mmol) and Boc20 (19.71 mL, 85 mmol). The dark solution was heated to reflux for 48 h, then cooled to RT, concentrated, and the residue purified via silica gel chromatography on the ISCO RF (liquid load, 330 g column, 0-10% EtOAc/Hexane over 30 min). Concentration of fractions containing product afforded 1 ,1-dimethylethyl (5-chloro-2-pyrazinyl)carbamate as a slightly yellow oil. This was used without further purification. Approximately 5 g of starting material was recovered. The rest of the material was a mixture of products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33332-29-5, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; HOANG, Tram, H.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2013/12500; (2013); 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. 4858-85-9, name is 2,3-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 4858-85-9

2- Amino-3 -chloro-pyrazine[00236] 2,3-Dichloropyrazine (2.5 g, 16.78 mmol) was dissolved in NH4OH (aq.) and the reaction mixture heated for 15 minutes at 150 C under microwave activation. Upon cooling a precipitate formed which was collected by filtration, washed with water and dried in vacuo at room temperature for 16 hours to give the title compound as a white, crystalline solid

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 4858-85-9.

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; PRICE, Paul Damien; MIDDLETON, Penny; WO2010/69684; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem