Tag: M.W=100-200

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. 138588-41-7, name is Pyrazine-2-carboximidamide hydrochloride, A new synthetic method of this compound is introduced below., Application In Synthesis of Pyrazine-2-carboximidamide hydrochloride

[0106] A mixture of diethyl 2-(2,4,6-trifluorophenyl)malonate (250 mg, 0.861 mmol), 2- pyrazinecarboxamidine hydrochloride (144 mg, 0.904 mmol, 1.05 equiv), and tributylamine (221 mu., [172 mg], 1.08 equiv) was stirred under nitrogen atmosphere at 180 C for 1 h in a sealed tube. The mixture was cooled to room temperature and treated with 1.0 N hydrochloric acid. The precipitates were collected by filtration, washed with water and dried to give 2-pyrazin-2-yl-5- (2,4,6-trifluorophenyl)pyrimidine-4,6-diol as a dark tan solid (163 mg), which was used directly in the next step. [0107] A mixture of 2-pyrazin-2-yl-5-(2,4,6-trifluorophenyl)pyrimidine-4,6-diol (163 mg) in phosphorous oxychloride (2.03 mL, 21.9 mmol, 43 equiv) and 2,6-lutidine (404 muIota_,, 3.51 mmol, 6.9 equiv) was heated at 1 10 C for 16 h in a sealed tube. The excess phosphorous oxychloride was removed in vacuo, and the resulting residue was dissolved in ethyl acetate. The organic layer was washed with water and saturated sodium chloride, dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography over silica gel, eluting with a gradient of 20% ethyl acetate in hexanes to 33% ethyl acetate in hexanes. Concentration provided 104 mg of the title compound as a light yellow solid (32% over two steps). -NMR (500 MHz; CDC13): delta 9.73 (s, 1H), 8.84 (s, 1H), 8.77 (s, 1H), 6.88-6.84 (m, 2H) ppm.

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; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; BALLATORE, Carlo; BRUNDEN, Kurt, R.; HOYE, Adam, T.; LEE, Virginia, M.y.; SMITH, Amos, B.; TROJANOWSKI, John, Q.; WO2014/47257; (2014); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 69816-35-9, 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. 69816-35-9, name is 6-(Trifluoromethyl)pyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

(a) 2-Iodo-6-trifluoromethylpyrazine A three liter flask was charged with a solution of 2-amino-6-trifluoromethylpyrazine (obtained by the method of J. L. Miesel, U.S. Pat. No. 4,293,552, 95% pure by HPLC analysis, 32.6 g, 0.20 mol) in chloroform (1000 mL). Freshly ground iodine (101 g. 0.40 mol) was added to give a dark purple solution. After 40 min, a solution of t-butyl nitrite (22.9 g, 0.20 mol) in chloroform (300 mL) was added dropwise over 1 h. During the addition, slow gas evolution was observed together with a mild exotherm (<10 C.) which was moderated with a cold water bath. After an additional 1 h at room temperature the reaction mixture was washed with saturated aqueous sodium sulfite (3*500 mL) to remove the excess iodine. The chloroform solution was dried over magnesium sulphate, filtered and concentrated on a Buchi to give 23 g of an orange oil. The crude product was purified by distillation from copper (40-80 mesh, 200 mg) to give 19.5 g of the title compound as a yellow oil; b.p. 50-56 C./0.6 mmHg; delta (360 MHz, CDCl3) 9.06 (1H, s, pyrazine-H), 8.86 (1H, s, pyrazine-H); m/e 274 (M+). The chemical industry reduces the impact on the environment during synthesis 6-(Trifluoromethyl)pyrazin-2-amine. I believe this compound will play a more active role in future production and life. Reference:
Patent; Merck Sharpe & Dohme Ltd.; US5384408; (1995); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 5424-01-1, name is 3-Aminopyrazine-2-carboxylic acid, molecular formula is C5H5N3O2, 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: C5H5N3O2

Add 3-aminopyrazine-2-carboxylic acid (50.0 g, 369.4 mmol) to a solution of N-bromosuccinimide (61.2 g, 377.3 mmol) and dimethylformamide (236.3 g, 3.2 mole) at 0 C. After 1 hour at room temperature, an orange solid is formed. Wash the solid residue with ethyl acetate (500 mL) and discarded it. Dry the organic phase with sodium sulfate, filter, and concentrate under reduced pressure to yield the title compound as a white solid (32.0 g, 146.7 mmol, 41%). ES/MS m/z (79Br/81Br) 217.1/219.0 (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 5424-01-1, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; CIFUENTES-GARCIA, Marta Maria; GARCIA-PAREDES, Maria Cristina; (34 pag.)WO2018/194885; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 16298-03-6, These common heterocyclic compound, 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, 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 B: Methyl 3-[(4-methyl-1-naphthoyl)amino]pyrazine-2-carboxylate; At 90 ¡ãC a solution of 4-methyl-1-naphthalenecarbonyl chloride (12 mmol) in CH2CICH2CI (20 mL) was slowly added into a solution of methyl 3-aminopyrazine-2- carboxylate (1.53 g, 10.0 mmol) and DMAP (100 mg) in CH2CICH2CI (100 mL) and pyridine (10 mL) during a period of six hours. The resulting reaction mixture was stirred at the same temperature overnight, and was then condensed, and extracted by EtOAc, washed by brine, dried over MgS04. Removal of solvents provided a crude product, which was purified by flash silica gel column using heptane/EtOAc (10: 0 to 0: 10) to give the title product as a solid (1.5 g, 47 percent) : 1H NMR (400 MHz, CDC13) No. 1H NMR (400 MHz, CD30D) 2.77 (s, 3H), 3.94 (s, 3H), 7.46 (d, J=8.0 Hz, 1H), 7.60 (m, 2H), 7.79 (d, J=8.0 Hz, 1H), 8.14 (d, J=8.0 Hz, 1H), 8.42 (m, lH), 8.50 (m, 1H), 8.64 (m,lH).

The synthetic route of 16298-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; WO2005/115986; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 875781-43-4, 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.

A solution of 21 (100 mg, 0.507 mmol) and 2 (84 mg, 0.507 mmol) in toluene and ethanol (4:1 mL) was added Na2CO3 (111.01 mg, 1.014 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd(dppf)Cl2 (20.7 mg, 0.025 mmol) was added to the reaction. The reaction was degassed and purged with nitrogen for another 10 min. The reaction was heated to 90 C. under sealed condition overnight, allowed to cool to RT, and diluted with chloroform. The organic layer was filtered through Celite and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted in 40% ethyl acetate in hexane as an off-white solid 22. MS-ES+ 264.8; 1H NMR (400 MHz, DMSO-D6) 22: 9.99 (bs, 1H), 9.40 (bs, 1H), 7.25 (bs, 1H), 7.08 (m, 1H), 7.00 (d, 1H), 6.42 (m, 2H), 6.21 (m, 1H), 5.71 (m, 1H).

Statistics shows that 2-Bromo-5H-pyrrolo[2,3-b]pyrazine is playing an increasingly important role. we look forward to future research findings about 875781-43-4.

Reference:
Patent; ARRIEN PHARMACEUTICALS LLC; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; Gangireddy, Paramareddy; Appalaneni, Rajendra P.; US2014/315909; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, 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 113305-94-5, Formula: C5H4N4

EXAMPLE 12 (?)-5-((4-Amino-8-(4-(2-cyanovinyl)-2,6-dimethylphenyl)quinazolin-2- yI)amino)pyrazine-2-carbonitrile- Compound 12 Synthesis of (?)-5-((4-amino-8-(4-(2-cyanovinyI)-2,6-dimethyIphenyl)quinazolin-2- yl)amino)pyrazine-2-carbonitrile (compound 12) [0274] Compound 2a (20 mg, 0.06 mmol), 5-aminopyrazine-2-carbonitrile (22 mg, 0.18 mmol, Ark Pharm Inc, AK-21935), N,N-diisopropylethylamine (62 mg, 0.47 mmol), (9,9- dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (3 mg, 0.006 mmol) and palladium (II) acetate (1 mg, 0.006 mmol) were combined under argon in N-methyl-2-pyrrolidone (1 mL). The reaction was heated at 120C in a sealed vessel for 3 hours. The reaction mixture was cooled down to room temperature and purified by reverse phase chromatography (0- 100% acetonitrile in water with 0.1% trifluoroacetic acid) to afford the TFA salt of compound 12. NMR (400 MHz, DMSO- 6) delta 8.98 (bs, 1 H), 8.36 (bs, 1 H), 7.85 – 7.28 (m, 6H), 6.59 (d, J = 15.6 Hz, 1H), 1.94 (s, 6H). LCMS (m/z) 419.3 [M+H], Tr = 1.89 min (LCMS method 2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Aminopyrazine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE AS CR, V.V.I.; JANSA, Petr; SIMON, Tetr; LANSDON, Eric; HU, Yunfeng, Eric; BASZCZYNSKI, Ondrejj; DEJMEK, Milan; MACKMAN, Richard, L.; (185 pag.)WO2016/105564; (2016); 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

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

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

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