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. 173253-42-4, name is 2-Amino-5-bromo-6-chloropyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Amino-5-bromo-6-chloropyrazine

In a pressure tube were mixed 2-amino-5-bromo-6-chloropyrazine (2.00 g, 9.60 mmol), 3-fluor-ophenylboronic acid (1.48 g, 10.55 mmol), sodium carbonate (2.03 g, 19.19 mmol) in a 4:1 mixture of 1 ,4-dioxane : water (25 mL). The reaction mixture was sparged with argon and Pd(PPh3)4 (0.22 g, 0.20 mmol) was then added. The mixture was sparged with argon shortly and the vessel was sealed and the reaction mixture was heated at 10000 for 20h. After that time the reaction mixture was cooled down to r.t. filtered through Celite pad diluted with AcOEt, or-ganic layer was washed with NaHCO3, brine and dried over Na2SO4. Then the mixture was concentrated under reduced pressure. The obtained residue was purified by flash chromatography on silica eluting with hexane : EtOAc (1:0 – 1:1) to lead to the title product as a light yellow solid(1 .82 g, 85%). ESI-MS: 224.00 [M+H].

The synthetic route of 173253-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SELVITA S.A.; BOBOWSKA (NEE WITKOWSKA), Aneta; GALEZOWSKI, Michal; NOWAK, Mateusz; COMMANDEUR, Claude; SZEREMETA-SPISAK, Joanna; NOWOGRODZKI, Marcin; OBARA, Alicja; DZIELAK, Anna; LOZINSKA, Iwona; DUDEK (NEE SEDLAK), Marcelina; JANIGA, Anita; REUS, Jacek; WRONOWSKI, Marek; ZASTAWNA, Magdalena; RADZIMIERSKI, Adam; SWIRSKI, Mateusz; ZACHMANN, Julian; FABRITIUS, Charles-Henry; PORTER, Rod; FOGT, Joanna; (276 pag.)WO2019/2606; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 762240-92-6, The chemical industry reduces the impact on the environment during synthesis 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, I believe this compound will play a more active role in future production and life.

General procedure: To the stirred reaction mixture of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyrazine hydrochloride(11) (300 mg, 1.32 mmol), TEA (0.55 mL, 3.95 mmol)and toluene (10 mL), substituted cyanates 12(a-e)/isocyanates12(f-j) (1.32 mmol) were added at ambient temperature.The reaction mass was agitated at 75-80 C until thecompletion of the reaction that was monitored by TLC. Thereaction mass was allowed to cool at ambient temperatureand it was washed sequentially with 3% aqueous HCl(5.0 mL) and then water (5.0 mL). The organic fraction wasconcentrated under vacuum at 50-55 C to obtain crudeproduct. It was purified by column chromatography using10-50% of EtOAc:hexane mixture as a mobile phase.

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-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mannam, Madhava Rao; Devineni, Subba Rao; Pavuluri, Chandra Mouli; Chamarthi, Naga Raju; Kottapalli, Raja Sekhara P.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 194; 9; (2019); p. 922 – 932;,
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. 1082843-70-6, name is 3,5-Dibromo-2-chloropyrazine, A new synthetic method of this compound is introduced below., SDS of cas: 1082843-70-6

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._Step 2. Preparation of 3-chloro-6-(5-chloro-2-fluoropyridin-4-yl)-N-((tetrahydro-2H-pyran- 4-yl)methyl)pyrazin-2-amineTo a degassed suspension of 6-bromo-3-chloro-N-((tetrahydro-2H-pyran-4- yl)methyl)pyrazin-2-amine (358 mg, 1.168 mmol), Na2C03 (1 .518 ml, 3.04 mmol) and 5- chloro-2-fluoropyridin-4-ylboronic acid (307 mg, 1 .752 mmol) in DME (5 ml) was added PdCl2(dppf).CH2Cl2 adduct (76 mg, 0.093 mmol) . The reaction mixture was capped in a flask and heated to 100 C for 4 hr an oil bath. The reaction mixture was diluted with EtOAc and washed with H20 saturated NaCI. The organic layer was dried Na2S04, filtered and concentrated. The crude oil/solid was purified column chromatography on silica gel (30%EtOAc/Hexane) to yield 3-chloro-6-(5-chloro-2-fluoropyridin-4-yl)-N- ((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine (160 mg, 0.448 mmol, 38.4 % yield), LCMS (m/z): 357.0 (MH+), retention time = 1.02 min.

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; 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

Adding a certain compound to certain chemical reactions, such as: 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, 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 41270-66-0, Computed Properties of C16H11ClN2

5-Chloro-2,3-diphenylpyrazine (300 gm), 4-isopropylaminobutanol (443 gm) were taken and then heated to 170 – 195 C, stirred for 10 hours to 12 hours and further cooled to 25- 30C. Then added water, extracted with methyl tert-butyl ether, dried the organic layer and concentrated to obtain the desired compound. Yield: 252 gm Chromatographic Purity (by HPLC): 99.01%

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; HONOUR (R&D); PARTHASARADHI REDDY, Bandi; RATHNAKAR REDDY, Kura; SUBHASH CHANDER REDDY, Kesireddy; VAMSI KRISHNA, Bandi; RAJENDAR REDDY, Kancharla; (25 pag.)WO2017/168401; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, molecular formula is C5H4BrN3O2, 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: 486424-37-7

Step 3 : 5-Bromo-3-(6-methyl-lH-benzo [d] imidazol-2-yl)pyrazin-2-amine[00141] A mixture of 3-amino-6-bromo-pyrazine-2-carboxylic acid (5.52g, 25.32 mmol), 4-methylbenzene-l,2-diamine (3.09g, 25.32 mmol), diethoxyphosphorylformonitrile (4.54, 27.85 mmol) and triethylamine (7.06 mL, 50.64 mmol) in DME (30 mL) was heated in the microwave at 170C for 60 minutes. The mixture was diluted with ethyl acetate, washed with water followed by aqueous aHC03 then brine. After drying over MgSC^, the mixture was decolourised with charcoal and filtered through silica gel. After concentration, the mixture was filtered to give gold coloured crystals (4.005g, 52% Yield). MS (ES+) 305.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 486424-37-7, its application will become more common.

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

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 622392-04-5 as follows. Safety of 2-Bromo-5-iodopyrazine

(1-((1-(trifluoromethyl)cyclobutyl)methyl)piperidin-4-yl)methanol (880 mg, 3.50 mmol) was dissolved in THF (30 mL). At 0 C., NaH (126 mg, 5.25 mmol) was added thereto, and stirred for 30 minutes. 2-bromo-5-iodopyrazine (1.09 g, 3.85 mmol) was added thereto, following with stirring at 55 C. for 10 hours. The reaction mixture was added with water, and extracted with EtOAc. The obtained organic layer was washed with saturated aqueous brine solution, dried over anhydrous MgSO4, and filtered. The filtrate was concentrated under reduced pressure. The obtained material was used without further purifying process

According to the analysis of related databases, 622392-04-5, the application of this compound in the production field has become more and more popular.

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

Adding a certain compound to certain chemical reactions, such as: 957230-70-5, name is 3,6-Dibromopyrazin-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 957230-70-5, Recommanded Product: 3,6-Dibromopyrazin-2-amine

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

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, 3,6-Dibromopyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

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

Electric Literature of 1458-01-1,Some common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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.

Intermediate A.1 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 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. C5H5CIN402 ESI Mass spectrum: m/z = 189 [M+H]+; m/z = 187 [M-H]”

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-diamino-6-chloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; KLEY, Joerg; FRATTINI, Sara; HAMPRECHT, Dieter; WO2015/7517; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 173253-42-4, 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. 173253-42-4, name is 2-Amino-5-bromo-6-chloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Copper iodine (190 mg, 1 mmol), triethylamine (16.7 ml, 120 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1.3 g, 1.6 mmol), and tetrahydrofuran (100 ml) were added to 5-bromo-6-chloropyrazin-2-amine (4.2 g, 20 mmol) obtained from Step 1, and the resultant was bubbled using nitrogen gas. Trimethylsilylacetylene (3.6 ml, 26 mmol) was added to the mixture, and the resultant was reacted at 80C for 2 hours. The reactant was concentrated under reduced pressure, followed by adding water. Thereafter, the resultant was extracted 3 times with ethyl acetate. The organic layer was collected, dried over magnesium sulfate, and then concentrated under reduced pressure. Thereafter, the residue was purified on a silica gel column using chromatography. The title compound (3.16 g, 70%) was obtained by eluting as a mixed solvent (5:1 v/v) of hexane and ethyl acetate. 1H NMR (500 MHz, CDCl3) delta 7.84 (s, 1H), 4.85 (s, 2H), 0.28 (s, 9H).

The synthetic route of 2-Amino-5-bromo-6-chloropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dongguk University Industry-Academic Cooperation Foundation; GONG, Young Dae; KWAK, Se Hun; LEE, Eun Sil; (32 pag.)EP3231800; (2017); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6966-01-4,Some common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, 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.

A solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (500 mg, 2.16 mmol), tetrakis(triphenylphosphine)palladium(0) (124 mg, 0.108 mmol) and sodium methanethiolate (306 mg, 4.31 mmol) in DMF (10 ml) was sealed in a nitrogen flushed pressure tube. The pressure tube was heated at 50 C for 2 h then allowed to cool to RT. The reaction mixture was diluted with EtOAc (30 ml) then washed with hydrochloric acid (1 M, 2 x 25 ml). A precipitate formed, which was removed by filtration. The filtrate was dried over MgS04 and evaporated. The crude material thus obtained was purified by flash column chromatography on C18 (60 g). The column was eluted with MeC iHiO + 0.1% formic acid using the following gradient (%MeCN, column volumes): 10%, 2 CV; 10-100%, 20 CV; 100%, 2 CV. The desired fractions were combined and evaporated to yield the product as a dark yellow solid (77 mg, 19%).1H NMR (250 MHz, DMSO-de) delta 12.89 (s, 1 H), 8.24 (s, 1 H), 7.25 (s, 2H), 3.30 (s, 3H). LC/MS (System A): m/z (ESI+) = 186 [MH+], Rt = 0.72 min, UV purity = 98%.

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem