Month: April 2021

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. 873-42-7, name is 2-Amino-3,5-dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 873-42-7

In a flask, under an inert atmosphere of argon, was added 3,5-dichloropyrazin-2-amine (7.0 g, 42.7 mmol), bis(triphenylphosphine)palladium(II) dichloride (3.0 g, 4.27 mmol) and THF (240 mL). The resulting mixture was allowed to stir for 1 h at RT. The intermediate from Step A (30 mL, 64 mmol) was added and the resulting solution was warmed at 35oC for 2 days. The reaction was then quenched by the addition of brine. The resulting solution was extracted with EtOAc (3X) and the organic layers combined, washed with brine, dried over anhydr. Na2SO4, and filtered. The residue was purified by silica gel chromatography with EtOAc:petroleum ether (5-20%) to afford the title compound.

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 873-42-7.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BERGER, Raphaelle; DONG, Guizhen; RAGHAVAN, Subharekha; YANG, Zhiqiang; (179 pag.)WO2017/200857; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 132426-19-8, name is 2-Bromo-1-(pyrazin-2-yl)ethanone, 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 132426-19-8, Recommanded Product: 132426-19-8

Step 1. 3-Amino-6-chloro-1-(ethoxycarbonyl)-2-(pyrazine-2-carbonyl)indole The title compound was prepared according to the procedure described in step 2 of Example 1 from 4-chloro-2-(ethoxycarbonylamino)benzonitrile (Example 1, step 1) and 2-(bromoacetyl)pyrazine (prepared according to the method of F. H. Case et al., J. Am.Chem.Soc., 1956, 78, 5842). 1H-NMR (CDCl3) delta: 9.26 (1H, d, J=1.5 Hz), 8.67 (1H, d, J=2.6 Hz), 8.56 (1H, dd, J=1.5, 2.6 Hz), 8.21 (1H, d, J=1.8 Hz), 7.55 (1H, d, J=8.4 Hz), 7.27 (1H, dd, J=1.5, 8.4 Hz), 6.18 (2H, br s), 3.87 (2H, q, J=7.0 Hz), 0.93 (3H, t, J=7.0 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-(pyrazin-2-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; US6300363; (2001); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 89464-87-9,Some common heterocyclic compound, 89464-87-9, name is 3-Methoxy-5-methylpyrazin-2-amine, molecular formula is C6H9N3O, 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.

c) Isobutylchloroformate (4.79 ml) was added to a stirred solution of 2-amino-3-methoxy-5-methylpyrazine (5 g) and pyridine (2.91 ml) in dichloromethane (10 ml) at ambient temperature. After 90 minutes the reaction mixture was diluted with dichloromethane (10 ml) and washed with 2M hydrochloric acid (3*20 ml), water (20 ml) and saturated sodium chloride solution (20 ml) and then dried (MgSO4). Volatile material was removed by evaporation to give a solid which was recrystallized from hexane to give isobutyl N-(3-methoxy-5-methylpyrazin-2-yl)carbamate (6.5 g); 1 H NMR (CDCl3): 1.0 (d, 6 H), 2.0 (m, 1 H), 2.4 (s, 3 H), 4.0 (d, 2 H), 4.02 (s, 3 H), 7.3 (s, 1 H), 7.8 (s, 1 H); mass spectrum (positive chemical ionisation (+ve CI)): 240 (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 3-Methoxy-5-methylpyrazin-2-amine, its application will become more common.

Reference:
Patent; Zeneca Limited; US5866568; (1999); A;,
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 14508-49-7 as follows. name: 2-Chloropyrazine

Step 1 To a solution of chloropyrazine (11.5 g, 0.1 mmol) in absolute ethanol (50 ml) was added anhydrous hydrazine (16 ml, 0.5 mmol) and the reaction mixture was refluxed for 3 h. The organics were removed in vacuo and the residue was extracted with benzene to give hydrazinopyrazine (4.2 g).

According to the analysis of related databases, 14508-49-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Syntex (U.S.A.) LLC; US6316464; (2001); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 330786-09-9, The chemical industry reduces the impact on the environment during synthesis 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

Step 3: ethyl 3,5-dimethoxypyrazine-2-carboxylate To a solution of methyl 3,5-dichloropyrazine-2-carboxylate (0.312 g, 1.51 mmol) in THF (4.5 mL) at room temperature was added sodium hydride (60% wt. dispersion, 0.199 g, 4.98 mmol) and methanol (0.200 mL, 4.94 mmol). The reaction mixture was stirred at room temperature for 30 min, diluted with EtOAc, and quenched with saturated NH4Cl. The reaction mixture was partitioned between brine and EtOAc. The aqueous phase was extracted with EtOAc (3*) and the combined organic extracts were washed with brine (1*), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (10% to 50% EtOAc in hexanes) gave ethyl 3,5-dimethoxypyrazine-2-carboxylate (0.314 g, 1.48 mmol, 98% yield) as an off white solid.

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 3,5-dichloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (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. 41270-62-6, name is 2-Chloro-6-phenylpyrazine, A new synthetic method of this compound is introduced below., Formula: C10H7ClN2

To a mixture of (S)-tert-butyl 2-amino-4-(((S)-2-fluoro-3-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoate (150 mg, 331 mumol) and 2-chloro-6-phenylpyrazine (53 mg, 276 mumol) was added to t-AmOH (3 mL) then was added 2.0M t-BuONa in THF (276 muL, 552 mumol) and t-BuXPhos Pd G3 (22 mg, 28 mumol) and the resulting mixture was heated to 100 C. for 5 h, cooled to rt, and then concentrated in vacuo to give the title compound that was used without further purification. LCMS (ESI+): m/z=607.2 (M+H)+

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; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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. Recommanded Product: 24241-18-7

A mixture of morpholine (50 mL) and 3,5-dibromo-2-aminopyrazine (12.50 g) was refluxed for 1 h until the reaction was complete by TLC analysis. The solution was cooled to room temperature andadded to a beaker containing ice water (300 mL) with continuous stirring. The solid was precipitated and filtered. After drying, 12.30 g of a yellow solid with a metallic luster was obtained (a yield of 96.1%). 1H-NMR (DMSO-d6) delta 7.70 (s, 1H), 6.28 (s, 2H), 3.85-3.62 (m, 4H), 3.04 (d, J = 4.0 Hz, 4H).

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Shan; Sun, Chengyu; Chen, Chen; Zheng, Pengwu; Zhou, Yong; Zhou, Hongying; Zhu, Wufu; Molecules; vol. 22; 2; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 74290-67-8, 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. 74290-67-8, name is 2-Amino-5-bromo-3-methylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-bromo-3-methylpyrazin-2-amine (400 mg, 2.127 mmol) in 1 ,4-dioxane (20 ml_) was added potassium carbonate (588 mg, 4.25 mmol), tert-butyl carbamate (748 mg, 6.38 mmol), N,N’-dimethyl-1 ,2-ethanediamine (37.5 mg, 0.425 mmol) and Cul (40.5 mg, 0.213 mmol). The reaction mixture was heated to 100 C and stirred for 16h. The reaction was allowed to cool to room temperature. The reaction mixture was quenched with water (100 ml_). The resulting solution was extracted with EtOAc (3 x 100 ml_) and the organic layers were combined, washed with brine (2 x 100 ml_), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford crude product as a brown solid (400 mg, 70 % pure, 58% yield). Used without further purification.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EVANS, Karen Anderson; HILFIKER, Mark A.; MARCUS, Andrew Peter; PLOTNIKOV, Nikolay Valeryevich; RALPH, Jeffrey Michael; (142 pag.)WO2019/193540; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine, 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. Computed Properties of C7H5ClN2

Compound C28 (150 mg, 0.500 mmol), 1-chloropyrrolo[1,2-a]pyrazine (76 mg,0.50 mmol), cesium carbonate (488 mg, 1.50 mmol), palladium(ll) acetate (12 mg, 50pmol), and di-teit-butyl [3,4, 5,6-tetramethyl-2?,4? ,6?-tri(propan-2-yl) biphenyl-2- yl]phosphane (47 mg, 98 pmol) were combined in 1,4-dioxane (3 mL), and the reaction was degassed with nitrogen for 5 minutes. After the reaction mixture had been heated to 120 00 in a microwave for 3 hours, it was cooled to room temperature and filteredthrough diatomaceous earth; the filter cake was rinsed with ethyl acetate. The combined filtrates were concentrated in vacuo and the crude residue was purified via silica gel column chromatography (Gradient: 0% to 100% ethyl acetate in heptane) to provide the desired product as a yellow oil. Yield: 159 mg, 0.38 mmol, 77%. LCMS m/z 417.2 [M+H]. 1H NMR (400 MHz, CDCI3) characteristic peaks oe 7.62 (dd, J=1.0, 4.7Hz, 1H), 7.46 (dd, J=1.4, 2.5 Hz, 1H), 7.40 (brs, 1H), 7.38 (brs, 1H), 7.21-7.14 (m, 2H),7.08 (d, J=4.9 Hz, 1H), 6.99-6.97 (m, 1H), 6.85 (dd, J=4.1, 2.7 Hz, 1H), 6.15 (dd, J=11.0, 2.1 Hz, 1H), 4.20-4.17 (m, 1H), 3.80 (dt, J=11.5, 2.5 Hz), 2.12 (5, 3H), 2.01 (5, 3H).

The synthetic route of 136927-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (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. 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H5ClN4

Intermediate b (5.0 g, 0.034 mol) was added to triethyl orthoformate (50 mL), and the reaction was carried out at 80 C. The reaction time was monitored with a plate. The reaction liquid was directly filtered with cold suction, and the filter cake was washed with petroleum ether. After the cake was dried, 4.8 g of a yellow powder was obtained with a yield of 90.1%.

According to the analysis of related databases, 63286-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangxi Science and Technology Normal University; Zhu Wufu; Zheng Pengwu; Liu Xiaobo; Xu Shan; Zhang Qian; Tang Qidong; Zhou Hualan; Wu Jinjin; Yuan Ping; Zhang Hongbo; (25 pag.)CN110407839; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem