Category: Pyrazines

Some common heterocyclic compound, 93049-39-9, name is 7-Chloropyrido[3,4-b]pyrazine, molecular formula is C7H4ClN3, 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. HPLC of Formula: C7H4ClN3

EXAMPLE 1117-[3-(Pyrrolidin-l-ylmethyl)phenyllpyrido[3,4-Z>lpyrazineA mixture of 3-(bromomethyl)phenylboronic acid (150 mg, 0.69 mmol), pyrrolidine (70 muL, 0.84 mmol) and potassium phosphate (440 mg, 2.10 mmol) in DME (3 mL) was heated at 8O0C in a sealed reaction tube for 16 h. The reaction mixture was cooled to room temperature. 7-Chloropyrido[3,4-d]pyrazine (110 mg, 0.69 mmol), Pd(PPh3)4 (40 mg, 0.035 mmol) and water (0.5 mL) were then added. The resulting mixture was purged with nitrogen for 5 minutes, sealed and heated at 850C for 16 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (5 mL) and filtered through Celite. The filtrate was concentrated to dryness and purified by preparative HPLC to give the title compound (12.0 mg, 6%) as a pale brown solid. 5H (CDCl3) 9.62 (IH, s), 9.02 (IH, d, J 1.78 Hz), 8.91 (IH, d, J 1.78 Hz), 8.37 (IH, s), 8.22 (IH, s), 8.13 (IH, dt, J 6.69, 2.04 Hz), 7.58-7.48 (2H, m), 3.96 (2H, s), 2.70-2.84 (4H, m), 2.03-1.79 (4H, m). LCMS (ES+) 291 (M+H)+, 9.83 minutes {Method 5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 93049-39-9, its application will become more common.

Reference:
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 59303-10-5, name is 2-Chloro-5-methylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Chloro-5-methylpyrazine

Example 8l-((2S,4R)-6-(l-(2-methoxyethyl)-lH-pyrazol-4-yl)-2-methyl-4-((5- methylpyrazin-2-yl)amino)-3, -dihydroquinolin-l(2H)-yl)ethanonel-((2S,4R)-4-Amino-6-(l-(2-methoxyethyl)-lH-pyrazol-4-yl)-2-methyl-3,4- dihydroquinolin-l(2H)-yl)ethanone (for a preparation see Intermediate 7) (150mg, 0.457 mmol), 2-chloro-5-methylpyrazine (147mg, 1.142 mmol), Davephos (71.9mg, 0.183 mmol), Pd2(dba)3 (84mg, 0.091 mmol) and sodium tert-butoxide (132mg, 1.370 mmol) were combined in 1,4-dioxane (4ml) and the mixture heated at 120C for 25min (microwave). The reaction mixture was partitioned between water (75ml) and DCM (3x 75ml). The organics were combined, dried (hydrophobic frit) and evaporated under vacuum. The resulting brown oil was dissolved in DMSO (3x 1ml) and purified by MDAP (formate x3). The solvent was evaporated under vacuum to give l-((2S,4R)-6-(l-(2-methoxyethyl)-lH-pyrazol-4-yl)-2- methyl-4-((5-methylpyrazin-2-yl)amino)-3,4-dihydroquinolin-l(2H)-yl)ethanone (91mg, 0.216 mmol, 47 % yield) as a yellow glass. LCMS (formate), Rt 0.75min, MH+ 421.

The synthetic route of 59303-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; AMANS, Dominique; DEMONT, Emmanuel, Hubert; JONES, Katherine, Louise; SEAL, Jonathan, Thomas; WALKER, Ann, Louise; WO2012/150234; (2012); 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. 54608-52-5, name is 2-Hydrazinopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H6N4

General procedure: 2.5. General preparation of dregamine andtabernaemontanine derivatives 3-12Dregamine/tabernaemontanine (1/2) (1 equiv.) was dissolved in MeOH (3 mL) with the suitablehydrazine/hydroxylamine (3 equiv.) and a catalytic amount of acetic acid. Themixture was stirred under reflux for 2-24 h. The reaction mixture was extractedwith EtOAc (3 x 50 mL). The organic layers were combined and dried (Na2SO4).The solvent was removed under vacuum at 40 C and the obtained residue waspurified by column chromatography 2.5.6. Tabernaemontanine pyrazine-2-ylhydrazone(8) Obtained from reaction of the compound 2 with 2-hydrazinopyrazine(Sigma-Aldrich Chemie GmbH, Riedstrasse D-89555, Steinhelm, Germany; 3 equiv).The mixture was left under reflux for 24 h. The residue was purified by flashcolumn chromatography (silica gel CH2Cl2/MeOH 1:0 to93:7) to afford 10 mg (0.022 mol, yield 36 %) of an amorphous orange powder. IR(NaCl) vmax 3526,1730, 1656 cm-1.1H NMR (400 MHz, MeOD) delta 9.15 (1H, s, H-3?), 8.67 (1H, bs, H-6?),8.51 (1H, bs, H-5?), 8.16 (1H, d, J = 8.0 Hz, H-9), 8.03 (1H, bs, N-H), 7.93 (1H, d, J = 8.0Hz, H-12), 7.80 (1H, t, J = 7.8 Hz, H-11), 7.66 (1H, t, J = 7.6Hz, H-10), 4.55 (1H, td, J = 8.0, 3.0 Hz, H-5), 3.84 (2H, m, H-6), 3.60(3H, m, H-14, H-15), 3.50 (2H, m, H-16, H-21a), 3.21 (3H, s, -COOMe),3.11 (3H, s, N-Me), 2.33 (2H, m, H-19), 2.19 (1H, m, H-21b), 2.10 (1H, m,H-20), 1.62 (3H, t, J = 7.3 Hz, H-18) ppm; 13C NMR (101 MHz,MeOD) delta 173.2 (-COOMe), 155.5 (C-3), 153.9 (C-2?), 142.7 (C-6?), 141.8(C-5?), 138.0 (C-13), 134.3 (C-3?), 131.0 (C-8), 124.6 (C-11), 119.9 (C-10),119.7 (C-9), 115.2 (C-7), 111.7 (C-12), 59.3 (C-5), 50.9 (-COOMe), 46.8(C-21), 43.6 (N-Me), 43.0 (C-20), 42.9 (C-16), 34.0 (C-15), 32.2 (C-14), 26.5(C-19), 19.4 (C-6), 13.1 (C-18) ppm. HRMS-ESI-TOF m/z calcd C25H30N6O2[M+H] + 447.2430, found 447.2510.

According to the analysis of related databases, 54608-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Paterna, Angela; Borralho, Pedro M.; Gomes, Sofia E.; Mulhovo, Silva; Rodrigues, Cecilia M.P.; Ferreira, Maria-Jose U.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 17; (2015); p. 3556 – 3559;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 6164-79-0, name is Methyl 2-pyrazinecarboxylate, molecular formula is C6H6N2O2, 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. Formula: C6H6N2O2

Methyl pyrazine-2-carboxylate (0.5g; 3.6mmol) was dissolved in THF (5mL), and 98% hydrazine (0.53mL; 11mmol) was added. The mixture was refluxed for 3h and cooled to rt. The resulting solid was filtered off, washed with THF and dried over P2O5 to give 0.28g (56%) of a white solid. Rf=0.53 (CHCl3/MeOH 10:1). mp 166-169C (lit. 167-169C) [64]. 1H NMR (300MHz, DMSO): delta 10.11 (s, 1H, NH), 9.12 (s, 1H, Ar), 8.82 (d, J=2.4Hz, 1H, Ar), 8.68 (d, J=2.4Hz, 1H, Ar), 4.65 (s, 2H, NH2). 13C NMR (75MHz, DMSO): delta 161.7, 147.4, 145.1, 143.7, 143.4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6164-79-0, its application will become more common.

Reference:
Article; Hru?kova, Kate?ina; Pot??kova, Eli?ka; Hergeselova, Tereza; Liptakova, Lucie; Ha?kova, Pavlina; Mingas, Panagiotis; Kova?ikova, Petra; ?im?nek, Toma?; Vavrova, Kate?ina; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 97 – 110;,
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Pyrazine | C4H4N2 – PubChem

Electric Literature of 58138-79-7,Some common heterocyclic compound, 58138-79-7, name is 2,6-Diiodopyrazine, molecular formula is C4H2I2N2, 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.

An oven-dried sealed tube was charged with 2-bromo-4-methyl-thiazole- 5-carboxylic acid 4-fluoro-benzylamide (1.0 g, 3.03 mmol, 1.0 equiv). The sealed tube was purged with nitrogen and Rieke zinc (10 mL, 10 g of zinc in 100 mL of tetrahydrofuran) was added. The reaction was heated in the microwave oven for 15 min 50352at 100 0C. Stirring was stopped and the remaining zinc was allowed to settle. The supernatant containing the zinc reagent was transferred via syringe to a solution of 2,6- diiodopyrazine (704 mg, 2.1 mmol, 0.7 equiv), Pd(PPh3)4 (175 mg, 0.2 mmol, 5 mol%) in tetrahydrofuran (2 mL) and dimethyl formamide (0.1 mL). The reaction mixture was purged with nitrogen for 10 min, then stirred at 140 0C for 20 hr. After cooling, the solvent was removed in vacuo and the crude product was purified by column chromatography [SiO2, ethyl acetate/heptane, 10:90 to 40:60, v/v] to afford 2-(6-iodo- pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid 4-fiuoro-benzylamide (100 mg, 7%). MS (M+H)+ = 455.1 , R1 = 1.53 min.

The synthetic route of 58138-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; XENON PHARMACEUTICALS INC; WO2008/24390; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19745-07-4, name is 2,5-Dichloropyrazine, 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 19745-07-4, Quality Control of 2,5-Dichloropyrazine

analogously to Synthesis Example 13, Step 1, starting with 2,5-dichloropyrazine: HPLC-MS: (m/z): 196.1 (M+H)+. 1-(6-Fluoropyrazin-2-yl)-1H-pyrazole-3-amine:

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, 2,5-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AG; Heilmann, Eike Kevin; Greul, Joerg; Trautwein, Axel; Schwarz, Hans-Georg; Adelt, Isabelle; Andree, Roland; Luemmen, Peter; Hink, Maike; Adamczewski, Martin; Drewes, Mark; Becker, Angela; Voerste, Arnd; Goergens, Ulrich; Ilg, Kerstin; Jansen, Johannes-Rudolf; Portz, Daniela; US2015/239847; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, 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: 875781-43-4

Step 1. (2-Bromo-5H-pyrrolo[2,3-b]pyrazine-5,7-diyl)dimethanol. To a stirred solution of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (116.5 g, 589 mmol) in dioxane (1.75 L) was added dropwise aqueous NaOH (590 mL, 1175 mmol, 2 M) at room temperature, then formaldehyde (481 mL, 5884 mmol, 37% aqueous solution) was added to the mixture at room temperature. After that, the resulting mixture was stirred at room temperature for 18 hours. TLC (petroleum ether/EtOAc, 2:1) showed starting material was consumed completely. The three batches were combined for workup together. The reaction mixture was evaporated to remove most of solvent. The residue was neutralized with 2 M HCl and extracted with EtOAc (1 L¡Á3), the combined organic layers were washed water (1 mL) and brine (1 mL), dried over Na2SO4 and concentrated to dryness, which was triturated with MTBE to give (2-bromo-5H-pyrrolo[2,3-b]pyrazine-5,7-diyl)dimethanol (450 g, 95.5%) as a yellow solid.

The synthetic route of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Thorarensen, Atli; Brown, Matthew Frank; Casimiro-Garcia, Agustin; Che, Ye; Coe, Jotham Wadsworth; Flanagan, Mark Edward; Gilbert, Adam Matthew; Hayward, Matthew Merrill; Langille, Jonathan David; Montgomery, Justin Ian; Telliez, Jean-Baptiste; Unwalla, Rayomand Jal; US2015/158864; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1209459-10-8, name is 2-Bromo-5-fluoropyrazine, 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 1209459-10-8, COA of Formula: C4H2BrFN2

(R)-N-(6-(1-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-1H-tetrazol-5-yl)pyridin-2-yl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-7-carboxamide (97 mg, 0.185 mmol), 2-bromo-5-fluoropyrazine (49.2 mg, 0.278 mmol), RuPhos (17.29 mg, 0.037 mmol), Pd(dba)2 (10.65 mg, 0.019 mmol) and Cs2CO3 (121 mg, 0.370 mmol) were combined in a vial. Toluene (0.842 ml) was added and the mixture was evacuated and back-filled with N2 three times. Heated under N2 at 80 C. overnight. The reaction was filtered through celite, rinsing with EtOAc. The filtrate was concentrated to give an orange gum. The crude sample was treated with conc. HCl/MeOH (1:10, 3 mL) at rt until the TBS group was cleaved. After concentration, the crude sample was purified by preparative HPLC (10% ACN/water to 90% ACN/water in ?40 min with 0.1% FA buffer) to give (R)-2-(5-fluoropyrazine-2-yl)-N-(6-(1-(1-hydroxypropan-2-yl)-1H-tetrazol-5-yl)pyridin-2-yl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-7-carboxamide (6 mg, 0.012 mmol, 6% yield).

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, 2-Bromo-5-fluoropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Enanta Pharmaceuticals, Inc.; Granger, Brett; Wang, Guoqiang; Shen, Ruichao; He, Jing; He, Yong; Xing, Xuechao; Ma, Jun; Long, Jiang; Wang, Bin; Or, Yat Sun; (121 pag.)US2020/157095; (2020); 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. 77112-53-9, name is Imidazo[1,2-a]pyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Safety of Imidazo[1,2-a]pyrazine-2-carboxylic acid

General procedure: Imidazo[1,2-a]pyrazine-2-carboxylic acid (5) (1.0 equiv.) Mukaiyama?s reagent and 2-chloro-1-methylpyridinium iodide (1.2 equiv.) were suspended in DMF (5.0 mL) under nitrogen atmosphere. Into the reaction mixture, aliphatic/aromatic amines (6a-l) (1.0 equiv.) and 1-methylimidazole (2.0 equiv.) were added. A homogeneous solution was formed after a gentle stirring. The reaction mixture was sealed in a microwave glass reactor and then irradiated by microwave oven at a constant temperature of 80 C with continuous stirring (1 min ramp, 15 min reaction time). After the reaction was completed, the solvent was removed through a rotary evaporator and the resulting residue was extracted by a biphasic system of 45 mL diethyl ether and 45 mL water. After the layer separation, the ether layer was dried by anhydrous sodium sulphate, followed by an evaporation of ether to get compounds 7a-l (Scheme-I).

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:
Article; Jyothi, Boggavarapu; Madhavi, Nannapaneni; Asian Journal of Chemistry; vol. 32; 1; (2020); p. 84 – 90;,
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 875781-43-4 as follows. COA of Formula: C6H4BrN3

Method AStep 1(2-Bromo-7-hydroxymethyl-pyrrolo [2,3 -b]pyrazin-5 -yl)-methanolTo a partial suspension of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (5.0 g, 25.2 mmol) in 1 ,4-dioxane (100 mL) was added 2.0 M aqueous NaOH (25 mL, 50.0 mmol) and 37% aqueous formaldehyde (19 mL, 252 mmol). The dark homogenous reaction mixture was stirred at room temperature overnight. The organics were evaporated under reduced pressure. The aqueous layer was neutralized with 1.0 M HC1 and extracted with EtOAc (2x). The combined organics were concentrated to afford 2.6 g of an orange solid. Upon standing, a thick brown precipitate formed in the aqueous layer. The precipitate was collected by filtration and dried. The brown solid was extracted with hot 10% MeOH/EtOAc (3 x 200 mL). The extracts were combined and evaporated to provide an additional 3.05 g of orange solid. Overall yield was 5.65 g (87%) of (2- bromo-7-hydroxymethyl-pyrrolo[2,3-b]pyrazin-5-yl)-methanol. 1H NMR (DMSO-d6, 400 MHz): delta (ppm) 8.43 (s, 1H), 7.96 (s, 1H), 6.71 (t, J=7.3 Hz, 1H), 5.59 (d, J=7.6 Hz, 2H), 5.10 (t, J=5.3 Hz, 1H), 4.66 (d, J=5.6 Hz, 2H).

According to the analysis of related databases, 875781-43-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Shaoqing; DE VICENTE FIDALGO, Javier; HAMILTON, Matthew Michael; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LI, Hongju; LOVEY, Allen John; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; LYNCH, Stephen M.; O’YANG, Counde; PADILLA, Fernando; SCHOENFELD, Ryan Craig; SIDDURI, Achyutharao; SOTH, Michael; WANG, Ce; WOVKULICH, Peter Michael; ZHANG, Xiaohu; WO2013/30138; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem