Tag: M.W=200-300

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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-5-iodopyrazine

Intermediate 31 (200 mg, 0.602 mmol), 2-bromo-5-iodopyrazine (172 mg, 0.602 mmol), 2M aqueous sodium carbonate solution (0.903 mL, 1.807 mmol) and anhydrous DMSO (2 mL) were charged to a sealed tube. The mixture was degassed by bubbling30 with nitrogen for 5 minutes before the addition of tetrakis(triphenylphosphine)palladium(0) (35 mg, 0.03 mmol). The mixture was sealed under nitrogen, then stirred at100C for 1 h. The reaction mixture was partitioned between water (25 mL) and EtOAc(50 mL), then the organic phase was washed with saturated aqueous NaHCO3 solution(10 mL) and brine (10 mL), dried over sodium sulfate and concentrated under vacuum. The residue was purified by FCC, eluting with a gradient of 17-100% EtOAc in heptane, to afford the title compound (160 mg, 42%) as an off white solid. oH (500 MHz, CDC13) 8.72-8.68 (m, 2H), 7.93 (s, 2H), 7.33-7.26 (m, 2H), 7.18 (d, J8.0 Hz, 1H), 7.13 (t, J7.55 Hz, 1H), 7.01 (t, J8.3 Hz, 1H), 6.82-6.52 (t, 1H), 4.36 (s, 2H), 2.61 (s, 3H).

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; UCB PHARMA S.A.; BENTLEY, Jonathan Mark; BROOKINGS, Daniel Christopher; BROWN, Julien Alistair; CAIN, Thomas Paul; CHOVATIA, Praful Tulshi; FOLEY, Anne Marie; GALLIMORE, Ellen Olivia; GLEAVE, Laura Jane; HEIFETZ, Alexander; HORSLEY, Helen Tracey; HUTCHINGS, Martin Clive; JACKSON, Victoria Elizabeth; JOHNSON, James Andrew; JOHNSTONE, Craig; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LEIGH, Deborah; LOWE, Martin Alexander; MADDEN, James; PORTER, John Robert; QUINCEY, Joanna Rachel; REED, Laura Claire; REUBERSON, James Thomas; RICHARDSON, Anthony John; RICHARDSON, Sarah Emily; SELBY, Matthew Duncan; SHAW, Michael Alan; ZHU, Zhaoning; WO2014/9295; (2014); 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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H3Br2N3

Intermediate Example 10-1 : Preparation of 6,8-dibromo-3-iodo-imidazo[1 ,2- ajpyrazineTo a stirred solution of intermediate example 9-1 (8.7 g g, 31.4 mmol) in DMF (210 mL) was added NIS (7.42 g, 33 mmol, 1 .05 eq) in one portion at rt. After 18 h stirring at 60C, the solvent was removed in vaccuo and the residue was taken up in DCM and washed with water and saturated sodium thiosulfate solution. The organic phase was dried over sodium sulphate, filtered and the solvent was evaporated to yield 9.46 g (74.8 %) 6,8-Dibromo-3-iodo-imidazo[1 ,2-a]pyrazine: 1H- NMR (300 MHz, CDCb): delta = 8.22 (1 H, s), 7.91 (1 H, s) ppm.

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 63744-22-9.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80229; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-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 117719-17-2, name: 5-Bromo-3-morpholinopyrazin-2-amine

Three batches of 5-bromo-3-morpholin-4-yl-pyrazin-2-ylamine (I-02, 2 g, 7.7 mmol), ethyl-3-bromo-4-oxo-piperidine-1-carboxylate (2.4 g, 10 mmol) and small amount of DME (~ 0.3 mL) were heated in parallel at 120 C for 4 h, until the reactants were consumed as determined by LCMS analysis. The three reaction mixtures were mixed and diluted with DCM (100 mL), washed with saturated aqueous solution of NaHC03 (2 x 200 mL) and brine (250 mL), dried over Na2S04 and concentrated in vacuo rendering a dark residue. The black residue was purified in two portions by Biotage flash column chromatography (cartridge 40M) eluting with a solvent system of EtOAc/cyclohexane (30%-75% of EtOAc), yielding the required intermediate I-03 (2 g, 21%) as cream solid

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; CENTRO NACIONAL DE INVESTIGACIONES ONC&Oacgr;LOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ ARISTEGUI, Sonsoles; GONZALES CANTALAPIEDRA, Esther; HERNANDEZ HIGUERAS, Ana Isabel; VARELA BUSTO, Carmen; WO2011/36461; (2011); A1;,
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. COA of Formula: C4H2BrIN2

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

Application of 6966-01-4, 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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

PdCl2(PPh3)2 (756.6 mg, 1.078 mmol) was added to a stirred suspension of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (5 g, 21.55 mmol), 2-(4-isopropylsulfonylphenyl)- 4,4,5,5-tetramethyl-l,3,2-dioxaborolane (8.022 g, 25.86 mmol) and 2M aqueous Na2CO3 (32.32 mL, 64.65 mmol) in 1 ,2-dimethoxyethane (60 mL) and the reaction heated at 90 C for 23 hours. The reaction mixture was cooled to ambient temperature and the resultant precipitate isolated by filtration. The solid residue was suspended in water and acidified with 1M HCl. The mixture was stirred for 20 minutes and the precipitate isolated by filtration and dried in vacuo at 50 C to give the sub-title compound as a green solid (3.04 g, 44% Yield). The filtrate was acidified further and extracted with EtOAc (x 3). The combined organic extracts were dried (MgS04), filtered and concentrated in vacuo to give a further portion of the sub-title product (1.13 g, 16% Yield). The products were combined to give the sub-title compound as green solid (4.17 g, 60% Yield). 1H NMR (400.0 MHz, DMSO) delta 1.18 (d, 6H), 3.45 (q, 1H), 7.72 (s, 2H), 7.92 (d, 2H), 8.35 (d, 2H), 9.01 (s, 1H) and 13.25 (br s, 1H) ppm; (ES+) 322.1.

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, Methyl 3-amino-6-bromopyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; YOUNG, Stephen, Clinton; STORCK, Pierre-Henri; VIRANI, Aniza, Nizarali; REAPER, Philip, Michael; PINDER, Joanne; WO2011/143423; (2011); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

1053656-22-6, name is 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, 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. HPLC of Formula: C14H21N3O4

0081] Method A-Step c: Preparation of tert-butyl 2-(hydroxymethyl)-5,6- dihydroi [0082] To a stirred solution of 7-tert-butyl 2-ethyl 5,6-dihydroimidazo[l,2-a]pyrazine – 2,7(8H)-dicarboxylate (50 mg, 0.17 mmol) in anhydrous THF (2 mL) was added L1AIH4 (13 mg, 0.34 mmol) batches at 0 C. The mixture was stirred at the same temperature for 30 minutes. TLC showed that the reaction was complete. The reaction mixture was quenched with Na2S04.10H2O. The mixture was dried over anhydrous Na2S04> filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH = 50: 1) to give a colorless oil (30 mg, 69.8%). *H NMR (400 MHz, CDC13) delta 6.81 (s, 1H), 4.67 (s, 2H), 4.57 (s, 2H), 3.95 (d, / = 5.2 Hz, 2H), 3.84 (s, 2H), 1.48 (s, 9H).

The synthetic route of 1053656-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHANG, Xiaohu; WO2014/113191; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 87486-34-8, A common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, molecular formula is C5H4Br2N2O, 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.

Step-(iii): Synthesis of 5-bromo- 1 -methyl-3-((4-(morpholine-4-carbonyl) phenyl) amino) pyrazin-2( 1H)-one:Intermediate-8b (0.5g, 1.87mmol), Intermediate-i (0.5 g, 2.49 mmol) in DMA (5 mL) were heated at 110¡ãC for i6hrs. Then the reaction mixture was poured over crushed ice, theprecipitate was filtered, dried under vacuum to get desired product as a yellow solid (400 mg,57percent); 1H NMR (400 MHz, DMSO-d6) oe 9.6 (s, 1H), 8.01 (d, 2H, J=8.8 Hz), 7.40 – 7.38 (m, 3H),3.6-3.45 (m, 1 1H); MS (ES) m/z 395 (M+1).

The synthetic route of 87486-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BORUAH, Anima; HOSAHALLI, Subramanya; PANIGRAHI, Sunil Kumar; WO2014/125410; (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. 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, A new synthetic method of this compound is introduced below., Product Details of 87486-34-8

To a solution of Cpd-2 (490 mg, 3 mmol) in iPrOH (20 ml) was added 3,5-dibromo-1- methylpyrazin-2(1H)-one (800 mg, 3 mmol). The reaction mixture was stirred at 90¡ãC for 24 h. The solvent was evaporated and purified by Gel to provide Cpd-3 (0.35 g, 30percent) as a yellow solid.

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; CHEN, Yi; WO2015/50703; (2015); 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. 426829-61-0, name is N-Benzyl-6-chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C11H10ClN3

To a stirred solution of benzimidazole (130mg, 1. LMMOL) in anhydrous DMF (5mL) at 0C under N2 was added sodium hydride (56mg, 60% dispersion in oil, 1. 45MMOL) in portions over 2 min. The mixture was stirred at 0C for 15 min and at RT for 60 min. To this was added a solution of (6-CHLORO-PYRAZIN-2-YL)- (L-BENZYL)-AMINE (220mg) in DMF (5mL) and the resulting mixture was then heated at reflux for 18h. The DMF was removed under reduced pressure and the residue diluted with chloroform. The organic layer was washed with water, dried (Na2SO4) and the solvent removed under reduced pressure to furnish the crude product. Column chromatography using dichloromethane-methanol (20: 1 < 10: 1) as eluant separated the product (100mg). H-N. m. r. (CD3) 8 4.66 (d, 2H, J= 5.7Hz, CH2), 5.56 (m, 1H, NH), 7.29-7. 39 (m, 7H, Ar-H), 7.78-7. 89 (m, 2H, Ar-H), 7.92 (s, 1H, pyraz-H), 8.16 (s, 1H, pyraz-H), 8.48 (s, 1H, benzimid-H2). m/z (ES) 302 (M++H). 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 426829-61-0. Reference:
Patent; CYTOPIA PTY LTD; WO2003/99811; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 486424-37-7, 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 486424-37-7 as follows.

CDI (2.23 g, 13.8 mmol) was added to a suspension of 3-amino-6-bromopyrazine-2- carboxylic acid (2.00 g, 9.17 mmol) in DMF (20 ml). The reaction was stirred at RT for 16h. The reaction mixture was cooled (0 00) then diluted with water (20 ml). The solid wascollected by filtration then washed with the minimum volume of water and cooled (0 00)MeCN then dried under vacuum to afford the product as a yellow solid (2.23 g, 86%).1H NMR (250 MHz, DMSO-d6) O 8.58- 8.52 (m, 2H), 7.96-7.82 (m, 3H), 7.15- 7.07(m, 1H). LC/MS (System A, MeOH quench): mlz (ESl) = 232 [Methyl ester M(79Br)H], 234 [Methyl ester M(81Br)H]), R = 0.87 mi UV purity = 95%.

According to the analysis of related databases, 486424-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; MCCARTHY, Clive; (108 pag.)WO2019/77340; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem