Tag: M.W=200-300

Some common heterocyclic compound, 193966-70-0, name is Methyl 5-(bromomethyl)pyrazine-2-carboxylate, molecular formula is C7H7BrN2O2, 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. Product Details of 193966-70-0

Example 112 5-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxymethyl}-pyrazine-2-carboxylic acid methyl ester The title compound was prepared in analogy to Example 101 from 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol (obtained in Example 19, step 5) and 5-bromomethyl-pyrazine-2-carboxylic acid methyl ester [CAS Reg. No. 193966-70-0]. MS (m/e)=516.3 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 193966-70-0, its application will become more common.

Reference:
Patent; Hunziker, Daniel; Lerner, Christian; Mueller, Werner; Sander, Ulrike Obst; Pflieger, Philippe; Waldmeier, Pius; US2010/249139; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1082843-70-6, name is 3,5-Dibromo-2-chloropyrazine, 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 1082843-70-6, Recommanded Product: 3,5-Dibromo-2-chloropyrazine

Step 1. Preparation of 6-bromo-3-chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2- amine.To a scintillation vial containing 3,5-dibromo-2-chloropyrazine (1 g, 3.67 mmol) and TEA (1 .024 ml, 7.34 mmol) was added MeCN (5 ml) and (tetrahydro-2H-pyran-4- yl)methanamine (0.557 g, 3.67 mmol). The homogenous reaction mixture was capped, and heated to 80 C in a oil bath for 4 hr. The reaction mixture was concentrated to dryness, diluted with EtOAc and sequentially washed with sat NaHC03, and sat NaCI. The organic layer was dried Na2S04, filtered and concentrated. The crude was purified by column chromatography on silica gel ( 20%EtOAc/Hexane) to yield 6-bromo-3-chloro- N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine (688 mg, 2.244 mmol, 61 .1 % yield), yield), LCMS (m/z): 308.0 (MH+), retention time = 0.94 min, and 6-bromo-5- chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine (55 mg, 0.179 mmol, 4.89 % yield), LCMS (m/z): 308.0 (MH+), retention time = 0.91 min.

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; NOVARTIS AG; ANTONIOS-MCCREA, William R.; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; MARTIN, Eric J.; PAN, Yue; LIN, Xiaodong; PFISTER, Keith B.; RENHOWE, Paul A.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/101062; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-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. Computed Properties of C6H6BrN3O2

Methyl beta-bromo-S-chloropyrazine-l-carboxylate (1-2)To a suspension of copper (II) chloride (3.48 g, 25.9 mmol, 2.0 equiv) in acetonitrile (43 mL) was added te/t-butylnitrite (3.06 mL, 25.9 mmol, 2.0 equiv). The reaction was heated to 600C for 30 minutes and then cooled to ambient temperature. To this suspension was added methyl 3-amino-6-bromopyrazine-2-carboxylate (Ll, 3.O g, 12.9 mmol, 1.0 equiv, commercially available from SynChem Inc.) as a solid in portions with gas evolution. The reaction mixture was heated to reflux for 18 hours and the reaction was cooled to ambient temperature. The reaction was partitioned between EtOAc and saturated NaHCO3. The organic phase was washed with NaHCO3 and dried over MgSO4. After concentration, the residue was purified by normal phase column chromatography (0 to 50% EtOAc in hexanes) to afford the product CL2) as a clear oil. ESI+ MS [M+H]+ C6H4BrClN2O2: 250.7 found, 250.9 required.

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; MERCK SHARP &; DOHME CORP.; MERCER, Swati, P.; ROECKER, Anthony, J.; WO2010/141275; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 622392-04-5, 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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Tert-butyl 4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridin-1-(2H)-yl]sulfonyl}tetrahydro-2H-pyran-4-carboxylate (10 g, 21.86 mmol, Gateway Chemical), 2-bromo-5-iodopyrazine (6.23 g, 21.86 mmol, Gateway Chemical), toluene (105 mL), ethanol (32 mL), 2M Na2CO3(aq) (64 mL), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with CH2Cl2 (1:1) (0.892 g, 1.1 mmol, Aldrich) were heated together under N2 at 73 C. for 3 hr and then cooled to ambient temperature overnight. The resulting mixture was diluted with ethyl acetate (300 mL) and deionized water (200 mL). The layers were separated, and the aqueous was back-extracted with ethyl acetate (100 mL). The combined ethyl acetate layers were washed with 150 mL each of sat. NaHCO3(aq) and brine, dried over MgSO4, filtered, and concentrated to afford an oil in vacuo. The oil was purified by chromatography on silica (heaxnes/ethyl acetate) to afford 7.68 g (72% yield) of solids.

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

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 886860-50-0, 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. 886860-50-0, name is 2-Amino-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Step 1. methyl 3-(5-aminopyrazin-2-yl)propiolate To a 5 mL of microwave vial was added 5-iodopyrazin-2-amine (100 mg, 0.452 mmol), methyl propiolate (161 muL, 1.810 mmol), potassium carbonate (125 mg, 0.905 mmol), copper (I) iodide (3.45 mg, 0.018 mmol), and THF (1508 muL). The reaction mixture was heated at 65 C. for 2 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo. The crude product was purified by flash chromatography (20% EtOAc in DCM) yielding methyl 3-(5-aminopyrazin-2-yl)propiolate (38%). LCMS (m/z): 178.4 (MH+), 0.48 min.

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

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

Related Products of 313340-08-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 313340-08-8 name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (200 mg), 3-chloro-4-methylsulfonylaniline (374 mg) and NMP (1 mL) was stirred at 230 C. for 1 hour using a microwave reaction system. Thereafter, trans-4-aminocyclohexanol (524 mg) was added to the reaction liquid and stirred at 190 C. for 30 minutes using a microwave reaction system. After cooling, the reaction liquid was partitioned using ethyl acetate and water, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; chloroform_methanol=10:0 to 30:1) to give a crude product. This product was heated with ethanol and washed to give a light yellow solid. To the light yellow solid, ethyl acetate was added and heated, and insoluble materials were separated by filtration and the filtrate was concentrated. After the filtrate was concentrated, the residue was heated and washed with ethanol to give 3-{[3-chloro-4-(methylsulfonyl)phenyl]amino}-6-ethyl-5-[(trans-4-hydroxycyclohexyl)amino]pyrazine-2-carboxamide (39 mg) as a light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; Waters Technologies Corporation; US2012/40968; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

25710-18-3, name is 2,3-Dichloropyrido[2,3-b]pyrazine, 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. Application In Synthesis of 2,3-Dichloropyrido[2,3-b]pyrazine

To a solution of 2,3-dichloro-pyrido [2,3-b] pyrazine (0. 5G) in methanol was added 0.3N solution of sodium methoxide (6. 5ML). The resulting mixture was heated to reflux for 4 hours allowed to cool and used in example (7b)

The synthetic route of 25710-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/21513; (2005); 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. 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C16H11ClN2

To a solution of 1.00 g of 2-chloro-5,6-diphenylpyrazine in 10 ml of methanol, 2.14 g of allylamine was added and the mixture was reacted in a sealed tube at 80C for 41 hours, followed by stirring at room temperature for 54 hours.. After the solvent was evaporated under reduced pressure, the reaction solution was combined with water, extracted with chloroform, dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure.. The residue was purified by silica gel column chromatography to obtain 330 mg of the desired compound as a pale yellow crystal having a melting point of 97 to 100C

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 41270-66-0.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1400518; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

132426-19-8, name is 2-Bromo-1-(pyrazin-2-yl)ethanone, 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. Recommanded Product: 2-Bromo-1-(pyrazin-2-yl)ethanone

To a solution of 1-(pyridin-2-yl)thiourea (0.129 g, 0.85 mmol) in DMF (7 mL), 2-bromo-1-(pyrazin-2-yl)ethan-1-one (0.20 g,0.99 mmol) and triethylamine (0.3 mL, 2.0 mmol) were added successively and heated the mixtureat 70C for 2 hours. After TLC showed completion, reaction mixture was diluted withEtOAc (20 mL) and washed with water (3 x 10 mL). The organic layer was dried over Na2SO4and concentrated. The resulting residue was purified by column chromatography (silicagel,100-200) and the desired product was eluted with 3% CH3OH in CH2Cl2. Concentration ofthe pure fractions afforded 58 (35 mg, 13.8% yield), as a greenish solid; 1H NMR: (400 MHz,DMSO-d6): delta 6.95 (d, J = 4.8 Hz, 1H), 7.11 (d, J = 8.4 Hz, 1H), 7.71-7.76 (m, 1H), 7.79 (s, 1H),8.32-8.33 (m, 1H), 8.58 (d, J = 2.4 Hz, 1H), 8.65-8.66 (m, 1H), 9.16 (d, J = 1.6 Hz, 1H), 11.57(s, 1H); 13C NMR: (300 MHz, DMSO-d6): 111.3, 114.5, 116.8, 117.0, 138.6, 146.8, 147.2, 152.0,158.8, 158.9, 159.0, 160.7; LCMS m/z (M+H) 256.04, purity 98.9%; HRMSMS ESI m/z calcdfor C12H9N5S (M+H)+ 256.06122, found 256.0634 (Delta 2.2 ppm).

The synthetic route of 132426-19-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kesicki, Edward A.; Bailey, Mai A.; Ovechkina, Yulia; Early, Julie V.; Alling, Torey; Bowman, Julie; Zuniga, Edison S.; Dalai, Suryakanta; Kumar, Naresh; Masquelin, Thierry; Hipskind, Philip A.; Odingo, Joshua O.; Parish, Tanya; PLoS ONE; vol. 11; 5; (2016);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 1458-01-1 as follows. Application In Synthesis of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate

3,5-Diamino-6-chloropyrazine-2-carboxylic acid A mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 l) 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]-

According to the analysis of related databases, 1458-01-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; HECKEL, Armin; Frattini, Sara; Hamprecht, Dieter; Kley, Joerg; US2013/109697; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem