Month: September 2021

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 1458-16-8 as follows. 1458-16-8

To a mixture under argon of 0.5 mmol of intermediate -if-,0.025 mmol of Cul and 1 mmol of potassium carbonate in a small thick glass reactor (Ace Tube) , are successively added 1 mL of isopropanol, 1 mmol of ethylene glycol and 0.75 mmol of thiophenol. The reactor is sealed with a Teflon stopper, placedunder magnetic stirring and heated two hours at 80C. The reaction mixture is cooled to room temperature and the thus obtained precipitate isolated through filtration, washed and recrystallized from hot methanol (yield : 88%)LCMS (IE, m/z): (M+1) 248; ?H NMR: oH ppm 400 MHz, DMSO: 7.19 -7.14 (3H, m, CHarom.) , 7.30-7.26 (2H, m, CHarom.) , 7.97 (1H, 5,CHarom)

According to the analysis of related databases, 1458-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PIERRE FABRE MEDICAMENT; KALOUN, El Bachir; BEDJEGUELAL, Karim; MORDANT, Celine; RABOT, Remi; TAMBURLIN, Isabelle; FOURNIER, Emmanuel; SCHMITT, Philippe; (74 pag.)WO2016/207345; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 330786-09-9,Some common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, molecular formula is C6H4Cl2N2O2, 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 Methyl 3,5-dichloropyrazine-2-carboxylate Jl (lOg, 48.3 mmol) was treated with sodium methoxide in MeOH (97 ml, 48.3 mmol) at RT for 3 hour. It was filtered and the filtrate was concentrated under reduced pressure. The residue was washed with water and dried to give compound J2 (9.79 g). LCMS for J2: m/e = 203 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,5-dichloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Wen-Lian; HE, Shuwen; WALSH, Shawn, P.; CUMMING, Jared, N.; (70 pag.)WO2016/118404; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-29-5, The chemical industry reduces the impact on the environment during synthesis 33332-29-5, name is 2-Amino-5-chloropyrazine, I believe this compound will play a more active role in future production and life.

General procedure: Method B is a modification of Method A and was performed under nitrogen atmosphere andwith extended work-up. Substituted benzoyl chloride (1.5 mmol, 1.2 equiv) was placed into the askunder nitrogen, diluted with dry DCM (5 mL) and dry pyridine (400 mg, 5 mmol, 4 equiv) was added.The mixture was mixed for 5 min under nitrogen. Then, 5-chloropyrazin-2-amine (162 mg, 1.25 mmol,1 equiv) dissolved in DCM (10 mL) was added dropwise over 10 min under nitrogen ow. The askwas closed by septum and stirred for additional 6 h. After reaction, the mixture was diluted with DCMto the final volume of 40 mL and washed with water (1 30 mL), 5% (m/m) aqueous NaHCO3 solution(1 30 mL), and brine (1 30 mL). The organic layer was dried over anhydrous Na2SO4 and adsorbedon silica (4 g) by evaporating the solvents under reduced pressure. Automated flash chromatographywas run using same conditions as described in Method A. If needed, the products were recrystallizedfrom hot EtOH (crystallization initiated by cooling and dropwise addition of cold water).

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

Reference:
Article; Zitko, Jan; Mindlova, Al?b?ta; Vala?ek, Ond?ej; Jand’ourek, Ond?ej; Paterova, Pavla; Janou?ek, Ji?i; Kone?na, Klara; Dole?al, Martin; Molecules; vol. 23; 9; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life. 1458-01-1

A mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 I) and NaOH (6 mol/l in water; 240 mL; 1 .44 mol) is refluxed for 3 h. The mixture is allowed to cool to r.t. and then neutralized by addition of hydrochloric acid (6 mol/l in water; approx. 240 mL). Water (200 mL) is added. The precipitate formed is filtered off with suction, washed with water and dried at 60°C. Yield: 99.6 g (107percent of theory). C5H5ClN4O2. ESI Mass spectrum: m/z = 189 [M+H]+; m/z = 187 [M-H]-.

The chemical industry reduces the impact on the environment during synthesis 1458-01-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HECKEL, Armin; BLUM, Andreas; HAMPRECHT, Dieter; KLEY, Joerg; WO2013/92674; (2013); 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. 19745-07-4, name is 2,5-Dichloropyrazine, A new synthetic method of this compound is introduced below., Safety of 2,5-Dichloropyrazine

Step C: (S)-3-(2-Fluoro-5-methyl-4-(methylsulfonyl)phenylamino)-l-(piperidin-4-yl)pyrrolidin-2-one (420 mg, 1.14 mmol) was dissolved in DMSO (10 mL) and 2,5-dichloropyrazine (203 mg, 1.36 mmol) and N-ethyl-N-isopropylpropan-2-amine (297 mu, 1.71 mmol) were added and the reaction heated to 110 °C overnight. The reaction was cooled to ambient temperature, water (60 mL) was added and the solids filtered. The solids were dissolved in CH2CI2, washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified over silica gel (70 to 100percent EtOAc in hexanes) to afford (S)-l-(l-(5- chloropyrazin-2-yl)piperidin-4-yl)-3-(2-fluoro-5-methyl-4-(methylsulfonyl)phenylamino)pyrrolidin-2-one (330 mg, 0.685 mmol, 60.2percent yield) as a pale yellow solid. Mass spectrum (apci) m/z = 482.2 (M+H).

The synthetic route of 19745-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; AICHER, Thomas Daniel; BENCSIK, Josef Roland; BOYD, Steven Armen; CONDROSKI, Kevin Ronald; FELL, Jay Bradford; FISCHER, John P.; HINKLIN, Ronald Jay; PRATT, Scott Alan; SINGH, Ajay; TURNER, Timothy M.; WO2011/146335; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 344940-70-1, name is 5-Bromo-3-phenylpyrazin-2-amine, 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 344940-70-1, Computed Properties of C10H8BrN3

Step B: 5-Amino-6-phenylpyrazine-2-carbonitrileTo a deoxygenated solution of 5-bromo-3-phenylpyrazin-2-amine (1.00 g, 3.20 mmol) in NMP (15 mL) was added dicyanozinc (1.13 g, 9.61 mmol) and Pd(dppf)Cl2 (0.262 g, 0.320 mmol). The resulting mixture was heated at 150 C for 3 h then cooled and partitioned between water (10 mL) and EtOAc (15 mL x 3). The combined organic layers were dried over Na2S04 and concentrated, and the residue was purified by silica gel column chromatography (PE/EtOAc = 10/1, 5/1, 2/1) to give the title compound. MS: m/z = 196.9 (M + 1).

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, 5-Bromo-3-phenylpyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; MITCHELL, Helen; FRALEY, Mark, E.; COOKE, Andrew, J.; CHEN, Yi-Heng; STUMP, Craig, A.; ZHANG, Xu-Fang; MCCOMAS, Casey, C.; SCHIRRIPA, Kathy; MCWHERTER, Melody; MERCER, Swati, P.; BABAOGLU, Kerim; MENG, Dongfang; WU, Jane; LIU, Ping; WOOD, Harold, B.; BAO, Jianming; LI, Chun Sing; MAO, Qinghua; QI, Zhiqi; (263 pag.)WO2015/148344; (2015); 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. 6270-63-9, name is Pyrazin-2(1H)-one, A new synthetic method of this compound is introduced below., Recommanded Product: Pyrazin-2(1H)-one

General procedure: The appropriate nucleophile (1 equiv.), the epoxide (1-3 equiv.) and a base (1-5 equiv.) were suspended in a solvent and the reaction mixture was heated under the stated conditions. (0735) The reaction was allowed to cool to rt, saturated NH4CI(aq) or water was added and the resulting mixture was extracted using DCM or EtOAc (x 3). The combined organic extracts were dried (phase separator or MgS04), concentrated under reduced pressure and the remaining residue was purified by flash chromatography to give the product.

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; ALMAC DISCOVERY LIMITED; ROUNTREE, James Samuel Shane; WHITEHEAD, Steven Kristopher; TREDER, Adam Piotr; PROCTOR, Lauren Emma; SHEPHERD, Steven David; BURKAMP, Frank; COSTA, Joana Rita Castro; O’DOWD, Colin; HARRISON, Timonthy; (333 pag.)WO2019/150119; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

38557-72-1, Adding a certain compound to certain chemical reactions, such as: 38557-72-1, name is 2-Chloro-3,5-dimethylpyrazine, 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 38557-72-1.

0.39 g of 2-chloro-3,5-dimethylpyrazine, 0.87 g of 2-(3-diphenylaminophenyl)-1,3,2-dioxaborolane which was obtained in Step 1, 0.30 g of sodium carbonate, 0.013 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2), 10 mL of water, and 10 mL of acetonitrile in a recovery flask equipped with a reflux pipe. The air in the flask was then replaced by argon. This reaction container was heated by microwave irradiation (2.45 GHz, 100 W) for 20 minutes. After that, the reaction container was cooled to 50 C. or lower. Then, water was added to the reaction solution, and the organic layer was subjected to extraction with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. After the drying, the solution was filtered. The solvent of this solution was distilled, and the obtained residue was purified by silica gel column chromatography using a mixed solvent of dichloromethane and ethyl acetate as a developing solvent, thereby obtaining the objective pyrazine derivative Hdm5dpappr (white powder, 11% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, produced by CEM Corporation). The synthesis scheme of Step 2 is shown by (b-1).

According to the analysis of related databases, 38557-72-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US2012/165523; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, 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. Recommanded Product: 75907-74-3

Reaction step 2-hydroxymethyl-3,5,6-trimethylpyrazine (9.5 g, 62.5 mmol) was sequentially added to a 250 mL three-necked flask,MnO2 (16.2 g, 187.5 mmol),Ethanol 100mL,Reflux 12h,TLC (petroleum ether – ethyl acetate 2: 1) detection reaction is almost complete,cool down,Filtering to obtain filtrate,Ethanol recovery under reduced pressure,To give a yellow solid,Purification by silica gel column chromatography (petroleum ether-ethyl acetate 4: 1)3,5,6-trimethylpyrazine-2-carbaldehyde as a pale yellow solid,The yield was 93.9%

The synthetic route of (3,5,6-Trimethylpyrazin-2-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anhui University of Chinese Medicine; Li, Jiaming; He, Guangwei; Chu, Zhaoxing; Huang, Weijun; Zhang, Yanchun; Xie, Di; Zuo, Jian; Liu, Huicai; (11 pag.)CN105237487; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, molecular formula is C4H2BrIN2, 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. Safety of 2-Bromo-5-iodopyrazine

t-butyl 4-(hydroxymethyl)piperidin-1-carboxylate (the product of synthesis step 1 of compound 431; 2.70 g, 12.54 mmol), 2-bromo-5-iodopyrazine (3.57 g, 12.54 mmol) and NaH (0.36 g, 15.05 mmol) were dissolved in 70 C. for THF (30 mL), following with stirring at the same temperature for 6 hours. The reaction mixture was added with water, and extracted with EtOAc. The organic layer was washed with saturated NH4Cl aqueous solution, dried over anhydrous MgSO4, and filtered. The filtrate was concentrated under reduced pressure. The concentrate was purified by column chromatography (SiO2, 12 g cartridge; EtOAchexane=0% to 20%), and concentrated to yield the title compound as white solid (4.04 g, 76%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 622392-04-5, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; Lee, ChangSik; Jang, TaegSu; Choi, DaeKyu; Ko, MooSung; Kim, DoHoon; Kim, SoYoung; Min, JaeKi; Kim, WooSik; Lim, YoungTae; US2015/166480; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem