Author: Jessica.F

Application of 1379338-74-5, The chemical industry reduces the impact on the environment during synthesis 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, I believe this compound will play a more active role in future production and life.

Intermediate 15: 1,1-Dimethylethyl (3R)-3-{[(7-chloropyrido[3,4-b]pyrazin-5-yl)amino]methyl}-3-fluoro-1-piperidinecarboxylate To a solution of 1,1-dimethylethyl (3R)-3-(aminomethyl)-3-fluoro-1-piperidinecarboxylate (2.32 g, 10.00 mmol) in N-methyl-2-pyrrolidone (NMP) (5 ml) was added 5,7-dichloropyrido[3,4-b]pyrazine (2 g, 10.00 mmol) and diisopropylethylamine (3.49 ml, 20.00 mmol). This was heated at 130 C. in a Biotage Microwave for 1 h. The reaction had not gone to completion and so further amine (380 mg) was added and it was again heated to 110 C. for 30 min in a microwave. The reaction was partitioned between ethyl acetate and aqueous ammonium chloride. The layers were separated and the aqueous was re-extracted with ethyl acetate. The combined organics were washed with brine and passed through a hydrophobic frit, and concentrated in vacuo to yield a crude brown oil. This was dissolved in DCM and purified through silica (50 g) eluting with an ethyl acetate/DCM gradient. Appropriate fractions were combined and concentrated in vacuo to give the title compound as a yellow-orange gummy solid (3.13 g) LCMS (Method B): Rt=1.24 min, MH+=395.8

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, 5,7-Dichloropyrido[3,4-b]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; Atkinson, Francis Louis; Atkinson, Stephen John; Barker, Michael David; Douault, Clement; Garton, Neil Stuart; Liddle, John; Patel, Vipulkumar Kantibhai; Preston, Alexander G.; Shipley, Tracy Jane; Wilson, David Matthew; Watson, Robert J.; US2014/5188; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 55557-52-3, 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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(i) (+-)-3-[(6R,8aS)-6-(hydroxymethyl)hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]pyrazine-2-carbonitrile A mixture of (+-)-(6R,8aS)-octahydropyrrolo[1,2-a]pyrazin-6-ylmethanol (1.05 g, crude), 3-chloropyrazine-2-carbonitrile (860 mg, 6.2 mmol), Et3N (1.5 mL) and THF (10 mL) was stirred at 80 C. overnight. After concentration, the crude product was directly subjected to silica gel column to afford pure product (1.03 g, 77%). 1H NMR (300 MHz, CDCl3): delta (ppm) 1.45 (m, 1H), 1.85 (m, 3H), 2.41 (m, 3H), 2.63 (m, 1H), 2.92 (dd, 1H), 3.18 (m, 2H), 3.53 (t, 1H), 3.79 (dd, 1H), 4.61 (m, 2H), 8.03 (s, 1H), 8.27 (s, 1H).

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-Chloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; NPS Pharmaceuticals; US2007/37816; (2007); 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. 4430-75-5, name is Octahydro-2H-pyrido[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C8H16N2

[00357] Step 1 : To a solution of 4-fluoronitrobenzene (0.55ml, 5.13 mmol) in AcN (6 mL), Octahydro-lH-pyrido[l,2-a]pyrazine (600 mg, 4.28 mmol) and DIEA (1.1 mL, 6.42 mmol) were added. The mixture was stirred at 75 C for overnight (in a sealed tube). The resulting mixture was cooled to room temperature and then concentrated. The crude product was purified by column chromatography (0-5% MeOH in DCM) to afford the desired product as yellow oil (1.03g, 92% yield). ESI-MS: calcd for (C14H19N302) 261, found 262 (MH+).

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; NANTBIOSCIENCE, INC.; TAO, Chunlin; POLAT,, Tulay; WEINGARTEN, Paul; NALLAN, Laxman; ARP, Forrest; WANG, Qinwei; HO, David; (129 pag.)WO2016/138527; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4744-50-7, A common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, molecular formula is C6H2N2O3, 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.

General procedure: A solution of 3,4,5-trimethoxyaniline (1.83 g, 10 mmol) and acid anhydride (10 mmol) in glacial acetic acid (15 mL) was heated under reflux for 12 h. After the evaporation of the reaction mixture to dryness under reduced pressure, the residue was neutralized by a solution of sodium bicarbonate (4%) until effervescence ceased. The precipitate obtained was washed with water, dried (P2O5) and recrystallized from an appropriate solvent.

The synthetic route of 4744-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Abdel-Aziz, Alaa A.-M.; Eltahir, Kamal E.H.; Asiri, Yousif A.; European Journal of Medicinal Chemistry; vol. 46; 5; (2011); p. 1648 – 1655;,
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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 24241-18-7

3,5-Dibromopyrazin-2-amine (10.0 g, 39.5 mmol) was suspended in 200 ml concentrated (32%) aqueous ammonia and the mixture was stirred at 130 00 in a pressure tube for 5 days. The mixture was allowed to cool, forming a precipitate. Thesolid was collected by filtration, washed with water and dried in vacuo to give 5.10 g(27.0 mmol, 68% yield) of the title compound as a pale brown solid. Purity 100%.1H NMR (300 MHz, DMSO-d6) oe ppm 7.20 (s, 1 H), 6.40 (br s, 2H), 6.05 (br s, 2H).UPLC/MS (3 mm) retention time 0.69 mm.LRMS: mlz 189, 191 (M+1, lxBr).

According to the analysis of related databases, 24241-18-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL, S.A.; AIGUADE BOSCH, Jose; CONNOLLY, Stephen; EASTWOOD, Paul Robert; ROBERTS, Richard Spurring; SEVILLA GOMEZ, Sara; CATURLA JAVALOYES, Juan Francisco; (110 pag.)WO2017/64068; (2017); 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. 344940-70-1, name is 5-Bromo-3-phenylpyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

To a solution of 5-bromo-3-phenylpyrazin-2-amine (26 mg, 0.1 mmol) and tert-butyl isopropyl(5-(tributylstannyl)thiazol-2-yl)carbamate (80 mg, 0.15 mmol) in DMF (0.4 mL) was added PdCl2(PPh3)2 (7 mg, 0.01 mmol) followed by DIPEA (0.044 mL, 0.25 mmol) and the reaction heated at 85 0C for 18h. The reaction mixture was cooled to room temperature and diluted with EtOAc (6 mL) and water (2 mL). the layers were separated and the aqueous layer further extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The product was isolated via column chromatography (SiO2, 25% EtO Ac/heptane) to afford the product (44 mg, 100% yield)

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 344940-70-1.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/155388; (2009); 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. 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3,5-Dichloro-6-ethylpyrazine-2-carboxamide

A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (3a, 90 mg, 0.409 mmol), 3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline (124 mg, 0.407 mmol), DIPEA (71 muL, 0.408 mmol) and 1,4-dioxane (3.6 mL) was stirred at 110 C for 19 h. After the mixture was cooled, water was added, and the resulting slurry was extracted with EtOAc. The organic layer was dried over Na2SO4, andconcentrated in vacuo. The residue was purified by silica gel columnchromatography (CHCl3/MeOH) to give 11 (110 mg, 55%) as an ochersolid. 1H NMR (CDCl3): delta 1.28 (3H, t, J=7.4 Hz), 1.72-1.99 (4H, m),2.29 (3H, s), 2.34-2.78 (11H, m), 2.85 (2H, q, J=7.5 Hz), 3.44-3.59(2H, m), 3.89 (3H, s), 5.38-5.57 (1H, m), 6.90 (1H, d, J=8.4 Hz),7.08-7.19 (1H, m), 7.32-7.41 (1H, m), 7.62-7.80 (1H, m), 10.66 (1H,s); MS (ESI) m/z [M+H]+ 488, 490.

According to the analysis of related databases, 313340-08-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iikubo, Kazuhiko; Kurosawa, Kazuo; Matsuya, Takahiro; Kondoh, Yutaka; Kamikawa, Akio; Moritomo, Ayako; Iwai, Yoshinori; Tomiyama, Hiroshi; Shimada, Itsuro; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1683 – 1692;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 143591-61-1, These common heterocyclic compound, 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]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.

3-bromo-8-chloroimidazo [1,2-a] pyrazine (1.33 g, 5.7 mmol),1- (2-methoxyethyl) -1H-pyrazole-4-amine (0.96 g, 6.8 mmol) was added to 15 mL of n-butanol,The temperature was raised to 120 C and reacted overnight.The solvent was removed by rotary evaporation, diluted with 30 mL of water, and extracted with ethyl acetate (20 mL * 3). The organic phases were combined,It was washed with 20 mL of saturated brine, dried over anhydrous sodium sulfate, and concentrated.Separation through a silica gel column gave 1.45 g of a pale yellow solid with a yield of 76%.

The synthetic route of 143591-61-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Xing Qingfeng; Ai Yixin; (85 pag.)CN110272426; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 313339-92-3, 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. 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

11360] tert-l3utyl (2R,3R)-2-methylpiperidin-3-ylcarbam- ate (310) (1.1 g, 5.1 mmol) was dissolved in THF (20 mE).the stirred solution was added DIEA (1.34 mE, 7.7 mmol), followed by 3,5-dichloropyrazine-2-cabonitrile (1.07 g,mmol). The reaction was stirred at room temperature forhout An additional amount of 3,5-dichioropyrazine-2-carbo- nitrile (200 mg, 1.2 mmol) was added, and the reaction was stirred for another hour. The solvent was removed under reduced pressure, and the residue was suspended in EtOAc. The organic mixture was washed with iN HC1 (aq), saturated NaHCO3(aq) and brine, dried, and concentrated in vacuo. The residue was then purified by silica flash column chromatography (EtOAc/hexanes) to give tert-butyl (2R,3R)-1 -(6- chioro-5-cyanopyrazin-2-yl)-2-methylpiperidin-3-ylcar- bamate (311), (1.54 g, 4.38 mmol, 86% yield).

The synthetic route of 3,5-Dichloropyrazine-2-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JIA, Zhaozhong J.; CHEN, Wei; THOMAS, William D.; US2015/158865; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 121246-96-6, These common heterocyclic compound, 121246-96-6, name is 3-Chloropyrazine-2-carbaldehyde, 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.

2,2,6,6-Tetramethylpiperidine (19.7ml, 117mmol) was added to a solution of n-butyl lithium (69.3ml of a 1.6M solution in hexane, lllmmol) in anhydrous THF (200ml) at -760C under an atmosphere of nitrogen, keeping the reaction temperature below -7O0C. The reaction mixture was stirred at -7O0C for 15 minutes then allowed to warm to O0C and stirred for a further 30 minutes before being cooled to -760C. 2-Chloropyrazine (1Og, 87.3mmol) was added dropwise such that the reaction temperature was kept below -7O0C. The reaction mixture was then stirred at -700C for 30 minutes. Ethyl formate (7.5ml, 98mmol) was then added such that the reaction temperature was kept below -700C. The reaction mixture was then stirred at -7O0C for 1.5 hours. Glacial acetic acid (13ml,.218mmol) was added at -7O0C and the mixture then allowed to warm to ambient temperature and the volatiles were removed by evaporation. The residue dissolved in ethanol (100ml) and hydroxylamine (6.83g, 105mmol) and triethylamine (24.2ml, 175mmol) were added. The mixture was heated at 500C for 18 hours and the volatiles were then removed by evaporation. The residue was dissolved in diethylether and any remaining insoluble material was removed by filtration. The filtrate was washed with water, the solvent removed from the organic layer by evaporation and the residue purified by chromatography on silica gel eluting with DCM, then with diethylether / DCM (1:4) and finally with EtOAc to give 3-chloropyrazine-2- carboxaldehyde oxime (5.21g, 37.9%) as a solid; NMR Spectrum 8.37 (s, IH), 8.50 (d, IH), 8.70 (d, IH), 12.25 (s, IH).

The synthetic route of 121246-96-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/106307; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem