Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 937669-80-2, name is 3-Bromopyrazine-2-carboxylic acid, 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 937669-80-2, COA of Formula: C5H3BrN2O2

In a 500 mL three-necked flask, 3-bromopyrazine-2-carboxylic acid (20.3 g, 0.1 mol) was dissolved in 200 ml of methanol, and 20 ml of concentrated sulfuric acid having a concentration of 98 wt% was added dropwise to the reaction solution.After stirring at room temperature for 12 hours, the reaction was quenched, the reaction was quenched with EtOAc (EtOAc)EtOAc.A mixed solvent of petroleum ether/dichloromethane (volume ratio of 2/1) was used as a rinse agent, and the yield was 83%.

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; South China Xietong Chuangxin Institute; Ying Lei; Hu Liwen; Huang Fei; Cao Yong; (22 pag.)CN108218891; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. category: Pyrazines

Example 13-3 Synthesis of 5-(N-Boc-N-2-picolylaminomethyl)pyrazine-2-carboxylic acid (Compound VII-6) The compound obtained in Example 13-2 (320 mg) was dissolved in DMF (6.4 ml) and potassium carbonate (383 mg) and 2-picolylamine (286 mul) were added. After the reaction for 17 hours, the reaction solution was concentrated, and added with water, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain a crude product of the title compound (444.1 mg) as brown syrup. The crude product was dissolved in dioxane (4 ml),and di-t-butyldicarbonate (0.35 ml) and 1 mol/l aqueous solution.of sodium hydroxide (4 ml) were added. After the reaction for 2 hours, the reaction solution was concentrated. After the addition of dilute hydrochloric acid, the residue was extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain the title compound (158.8 mg) as a light brown solid. MS(FAB,Pos.):m/z=345[M+1]+

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; Kureha Chemical Industry Co., Ltd.; EP1273571; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, 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 6966-01-4, category: Pyrazines

To the solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (10.0 g 43.1 mmol) in MeOH (70 mL) was added a solution of Li OH (9.0 g, 215 mmol) in water (70 mL). The mixture was stirred at 90 C for 3 hours. The reaction mixture was cooled to rt and acidified to PH = 4-5 with HC1 (2 M). The mixture was filtered to afford 7.4 g of 6 (79 %) as yellow solid. (0170) [0033] LC-MS (M+l): 218.0; 1H MR (400 MHz, DMSO-d6) delta 8.39 (s, 1H), 7.59 (br, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-6-bromopyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; MERRIMACK PHARMACEUTICALS, INC.; DRUMMOND, Dary| C.; GENG, Bolin; KIRPOTIN, Dmitri B.; TIPPARAJU, Suresh, K.; KOSHKARYEV, Alexander; ALKAN, Ozan; (142 pag.)WO2017/123588; (2017); A1;,
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 6966-01-4 as follows. Recommanded Product: Methyl 3-amino-6-bromopyrazine-2-carboxylate

Example 10 : 3-Amino-6-anilino-N-(2-methoxyphenyl)pyrazine-2-carboxamide(Compound II-3)SCHEME XCompound 11-3METHOD J:Step 1: 3-Amino-6-anilino-pyrazine-2-carboxylic acid[00167] Methyl 3-amino-6-bromo-pyrazine-2-carboxylate (1 g, 4.310 mmol) , aniline (401.4 mg, 392.8 mu, 4.310 mmol), sodium t-butoxide (952.7 mg, 9.913 mmol), Pd2(dba)3 (197.3 mg, 0.2155 mmol) and DavePhos (84.81 mg, 0.2155 mmol) were taken into toluene (10 mL) and heated at reflux under an atmosphere of nitrogen. The reaction mixture was cooled to ambient temperature and partitioned between EtOAc/saturated aqueous aHC03. The resultant precipitate was isolated by filtration and the aqueous layer extracted with EtOAc (x 3). The aqueous layer was acidified with 1M HCl and the resultant precipitate was isolated by filtration and combined with the previous precipitate to give the sub-title product as a beige solid (337 mg, 34% Yield). ‘H NMR (400.0 MHz, DMSO) delta 6.83 (t, 1H), 7.21- 7.25 (m, 2H), 7.69 (d, 2H), 8.10 (s, 1H), 9.07 (s, 1H) ppm; MS (ES+) 231.0.

According to the analysis of related databases, 6966-01-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; KNEGTEL, Ronald, Marcellus, Alphonsus; O’DONNELL, Michael; REAPER, Philip, Michael; WO2011/143419; (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. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate

General procedure: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.

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:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1082843-72-8, These common heterocyclic compound, 1082843-72-8, name is 6-Bromo-3-chloropyrazin-2-amine, 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.

6-Bromo-3- chloropyrazin-2-amine (2000 mg, 9.59 mmol) was dissolved in DCM (48 ml) followed by triethylamine (3.99 ml, 28.78 mmol), di-tert-butyl dicarbonate (4188. 12 mg, 19.19 mmol), and N,N-dimethylpyridin-4-amine (87.91 mg, 0.72 mmol). The reaction was allowed to stir at room temperature for ovemight. The crude material was washed with water, dried, filtered and concentrated. The crude material was dissolved in minimal DCM and loaded onto a 25 g prepacked silica loader and eluted off a 40 g column using 0-30% MeOH/DCM. The title compound XI was isolated and identified by LCMS and NMR. The product was a mix of mono and bis boc-protected material, mainly bis boc-protected as observed by NMR.

The synthetic route of 1082843-72-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; DI PAOLO, Julie, A.; LIN, Joseph, Haw-Ling; LIN, Shao-Lee; (86 pag.)WO2016/172117; (2016); 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. 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, A new synthetic method of this compound is introduced below., Computed Properties of C9H11BrN2O3

Step 3 3-(2-Ethylpyrid-3-ylamino)-6-methyl-1-(ethoxycarbonylmethyl)pyrazinone A mixture of 2-ethyl-3-aminopyridine (0.35 g, 2.8 mMol, 2 eq) from step 2 above and 3-bromo-6-methyl-1-(ethoxycarbonylmethyl)pyrazinone (0.39 g, 1.4 mMol) in 1 mL of nitrobenzene was heated at 200 C. for 2 h. The reaction was concentrated in vacuo and the residue purified by flash silica gel chromatography using 1% methanol in methylene chloride as an eluent to afford the title compound as a yellow oil that crystallizes upon sitting. (0.058 g; HPLC RT=4.45 min, method A).

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 & Co., Inc.; US6610692; (2003); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 63744-22-9, A common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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.

[0303] 6-Bromo-N-(4-(4-(oxetan-3-yI)piperazin-1-yl)-3-(2-((tetrahydro-2H- pyran-2 yl)oxy)ethoxy)phenyl)imidazo [1,2-a]pyrazin-8-amine XXV: To a solution of 4-(4-(oxetan-3-yl)piperazin-1-yl)-3-(2-((te1rahydro-2H-pyran-2-yl)oxy)emoxy)aniline XXIV (619 mg, 2.17 mmol) and 6,8-dibromoimidazo[1,2-a]pyrazine (601 mg, 2.2 mmol) in IPA (15 mL) was added N,N-Diisopropylethylamine (0.95 ml, 5.43 mmol). The mixture was stirred at 110 C for 16 h. After this time, DCM (10 mL) and sat aqueous NaHC03 (15 mL) were added. The aqueous layer was separated and extracted with DCM (2 10 mL). The combined organic extracts were washed with brine (10 mL) and dried over sodium sulfate. The resulting residue was purified by column chromatography ISCO Rf (24 g column) eluting with a gradient of 100% DCM – 60:35:5 DCM:Et20:MeOH to provide 6-bromo-N-(4-(4-(oxetan-3-yl)piperazin-1-yl)-3- (2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl)imidazo[ 1,2-a]pyrazin-8-amine XXV (1.2 g, quant).

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; GILEAD SCIENCES, INC.; BLOMGREN, Peter, A.; CLARKE, Astrid; CURRIE, Kevin, S.; DI PAOLO, Julie; KROPF, Jeffrey, E.; LEE, Seung, H.; LO, Jennifer, R.; MITCHELL, Scott, A.; SCHMITT, Aaron, C.; SWAMINATHAN, Sundaramoorthi; XIONG, Jin-Ming; XU, Jianjun; ZHAO, Zhongdong; (169 pag.)WO2016/10809; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63744-22-9,Some common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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.

To 4-(4-(oxetan-3-yl)piperazin-1-yl)aniline II (2.00 g, 8.57 mmoles), hunig’s base (3.29 mL) and 6,8-dibromoimidazo[1,2-a]pyrazine (2.37 g, 8.57 mmoles) was added in DMF (43 mL). The reaction was stirred at 85 C. in a pressure tube for overnight. The material was quenched with saturated sodium bicarbonate, extracted with DCM (120 mL*3) and the organic layers were combined and washed with water (120 mL*3), dried over anhydrous sodium carbonate and concentrated. The crude material was purified using a 120 g Isco column and eluted off using a stepwise gradient of 0-60% (10% MeOH/DCM). The desired fractions were combined and concentrated to provide the title compound III.

The synthetic route of 63744-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Lo, Jennifer R.; Mitchell, Scott A.; Schmitt, Aaron C.; Xiong, Jin-Ming; Xu, Jianjun; Zhao, Zhongdong; US2015/175616; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 957230-70-5, 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. 957230-70-5, name is 3,6-Dibromopyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of compound D as desc?bed in the general reaction scheme; 5,8-DiotabromoiotamiotadazofJ ,2- ajpyrazine.[00250] Bromoacetaldehyde diethyl acetal (49mL, 326mmol) and 48% hydrobromic acid is heated to reflux for 1 5h, then poured into propan-2-ol (60OmL) and quenched with NaHCO3. After filtering, 2,5-dibromo-3-aminopyrazme (41.34g, 163mmol) is added to the solution and heated at reflux overnight. The reaction is cooled and solvents removed in vacuo, followed by addition of aq NaHCO3 and extraction with EtOAc. The organic phase is dried over MgSO4, filtered, and concentrated in vacuo to afford a brown solid. 1H NMR (250MHz, CDCl3) delta(ppm)7.86 (IH, s), 7 93-7.94 (IH, d), 7.98-7.99 (IH, d), m/z (APCI) 278 (M+H)+; m.p 132-135C

The chemical industry reduces the impact on the environment during synthesis 3,6-Dibromopyrazin-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem