Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 173290-17-0, name is Methyl 3-iodopyrazine-2-carboxylate, 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 173290-17-0, SDS of cas: 173290-17-0

3-Iodopyrazine-2-carboxylic acid methyl ester (0.37 g, 1.4 mmol, Reference compound No.15-1), 4-pyridinemethanethiol hydrochloride (0.24 g, 1.5 mmol) and potassium carbonate (0.41 g, 3.0 mmol) were suspended in N,N-dimethylformamide (10 mL), then the mixture was stirred at 60C for 1 hour. The reaction mixture was diluted with ethyl acetate (70 mL), and washed with water (100 mL) twice and brine (70 mL) twice. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was filtered off with diisopropyl ether to give 0.25 g of the title reference compound as a pale cinnabar solid. (Yield 69%)1H-NMR(500MHz,CDCl3)delta 4.03(s,3H),4.37(s,2H),7.35(dd,J = 4.3,1.5 Hz,2H),8.39(d,J = 2.1 Hz,1H), 8.52(dd,J = 4.3,1.5 Hz,2H),8.53(d,J = 2.1 Hz,1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-iodopyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SANTEN PHARMACEUTICAL CO., LTD.; EP1602647; (2005); 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. 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,5-Dichloro-6-ethylpyrazine-2-carboxamide

A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (3a,503 mg, 2.29 mmol), 2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline (699 mg, 2.30 mmol), DIPEA (0.78 mL, 4.56 mmol) and 1,4-dioxane (10 mL) was stirred at 110 C for 25 h. After the mixture was cooled to room temperature, saturated aqueous NaHCO3 solution was added, and the resulting slurry was extracted with CHCl3. The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (CHCl3/MeOH/28% aqueous NH3=100:0:0 to90:9:1). The resulting product was washed with EtOAc, filtered and dried in vacuo at 50 C to give 9 (701 mg, 63%) as an orange solid. 1HNMR (DMSO-d6): delta 1.25 (3H, t, J=7.4 Hz), 1.43-1.59 (2H, m),1.77-1.91 (2H, m), 2.14 (3H, s), 2.20-2.72 (11H, m), 2.79 (2H, q,J=7.5 Hz), 3.64-3.75 (2H, m), 3.85 (3H, s), 6.51 (1H, dd, J=2.4, 8.8 Hz), 6.65 (1H, d, J=2.4 Hz), 7.83 (1H, d, J=1.6 Hz), 8.04 (1H, d,J=8.8 Hz), 8.12 (1H, d, J=1.6 Hz), 11.11 (1H, s); MS (ESI) m/z[M+H]+ 488.

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; 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

Application of 63744-22-9,Some common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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.

(R)-(4-(4-((6-Bromoimidazo[1,2-a]pyrazin-8-yl)amino)phenyl)morpholin-2-yl)methanol XVII In a 250 mL round bottom flask equipped with a condenser was placed 6,8-dibromoimidazo[1,2-a]pyrazine (2000 mg, 7.22 mmol) and added 30 mL isopropanol followed by N,N-diisopropylethylamine (2.52 ml, 14.44 mmol) and (R)-(4-(4-aminophenyl)morpholin-2-yl)methanol (1504.12 mg, 7.22 mmol). The reaction was heated to reflux (oil bath 95 C.) overnight. The reaction was cooled and precipitates were collected by filtration and washed with isopropanol followed by hexanes to give the desired compound XVII.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6,8-Dibromoimidazo[1,2-a]pyrazine, its application will become more common.

Reference:
Patent; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Lo, Jennifer R.; Mitchell, Scott A.; Schmitt, Aaron C.; Xiong, Jin-Ming; Xu, Jianjun; Zhao, Zhongdong; US2015/175616; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1458-01-1, 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. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.

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-diamino-6-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H2BrIN2

EXAMPLE 50A (exo)-3-(5-Iodo-pyrazin-2-yloxy)-8-methyl-8-aza-bicyclo[3.2.1]octane Under N2, the mixture of product from 7C (0.42 g, 3.0 mmol) was treated with potassium t-butoxide (Aldrich, 0.32 g, 3.3 mmol) in THF (anhydrous, Aldrich, 50 mL) at ambient temperature for 1 hours. The product of Example 41B (1.00 g, 3.5 mmol) and was added. The mixture was stirred at ambient temperature for 4 hours and quenched with water (5 mL). The mixture was concentrated and the residue was purified by chromatography (150 g SiO2, EtOAc:MeOH:NH3.H2O, 90:10:1, Rf. 0.40) to provide the title compound. 1H NMR (300 MHz, CD3OD) delta 1.90-2.25 (m, 4H), 2.31-2.60 (m, 4H), 2.84 (s, 3H), 3.94-4.11 (m, 2H), 5.32-5.57 (m, 1H), 8.06 (d, J=1.36 Hz, 1H), 8.42 (d, J=1.36 Hz, 1H) ppm; MS (DCI/NH3) m/z 346 (M+H)+.

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; Ji, Jianguo; Li, Tao; Lynch, Christopher L.; Gopalakrishnan, Murali; US2008/45539; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, molecular formula is C8H11BrN4O, 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. Application In Synthesis of 5-Bromo-3-morpholinopyrazin-2-amine

To a solution of Intermediate 1-02 (150 mg, 0.58 mmol) in Toluene (6.8 mE), 2-chloro-1,1-dimethoxypropane (0.758mE, 5.8 mmol) and p-toluenesulfonic acid (18 mg, 0.09 mmol) were added. The reaction mixture was refluxed for 24 hand additional amounts of 2-chloro-1 , 1-dimethoxypropane (10 eq) and p-toluenesulfonic acid (0.16 eq) were added. The reaction mixture was refluxed for 15 h and the solvent was removed. The residue was purified by column chromatography (Isolute 10 g; AcOEt-cyclohexane 0:100 to 50:50) to give the Intermediate 1-70 (55 mg, 32%) as a beige solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 117719-17-2, its application will become more common.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); Serrano Marugan, Manuel; Pastor Fernandez, Joaquin; Martinez Gonzalez, Sonia; Ortega Molina, Ana; Bischoff, James R.; Oyarzabal Santamarina, Julen; (220 pag.)US9993554; (2018); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)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. Application In Synthesis of 2-Bromo-5-(trifluoromethyl)pyrazine

To a suspension of Example 3B (0.08 g, 0.249 mmol) in N,N-dimethylformamide (0.5 mL, 6.46 mmol) were added N,N-diisopropylethylamine (0.174 mL, 0.996 mmol) and 2- bromo-5-(trifluoromethyl)-pyrazine (0.068 g, 0.299 mmol). The reaction mixture was stirred overnight at 90 C, and then it was concentrate under reduced pressure at 50 C. The residue was purified by flash column chromatography on silica gel (12 g) eluted with heptane and ethyl acetate (0 to 100%) to give 40 mg of the title compound (37.3% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.78 (s, 1H), 8.59 (s, 1H), 8.44 (s, 1H), 7.99 (s, 1H), 7.55 (d, J = 8.8 Hz, 1H), 7.27 (d, J = 2.8 Hz, 1H), 6.99 (dd, J = 9.0, 2.9 Hz, 1H), 4.51 (s, 2H), 2.37 (s, 6H); 19F NMR (376 MHz, DMSO-d6) delta ppm -64.83, -114.06; MS (ESI+) m/z 447 (M+H)+.

The synthetic route of 1196152-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-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 117719-17-2, Recommanded Product: 5-Bromo-3-morpholinopyrazin-2-amine

A mixture of 5-bromo-3-morpholin-4-yl-pyrazin-2-ylamine (0.3 g, 1 eq), methyl 4- oxobutanoate (182 mu, 1.5 eq), 1 , 1 ,3,3-tetramethylbutyl isocyanide (305 mu, 1 .5 eq) and ZrCL, (54 mg, 0.2 eq) in PEG-400 (3 mL) was heated at 50 C under open air for 20 h and 24 h more. On cooling, H20 (60 mL) was added and the mixture was extracted with EtOAc (3 x 50 mL). The organics were dried, filtered and evaporated and the residue was purified by automated chromatography (Biotage, eluent: 20% to 40% EtOAc in Cyclohexane) to give the expected product 1-14 (155 mg, 26% yield) as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-3-morpholinopyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONC&Oacgr;LOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ ARISTEGUI, Sonsoles; GONZALES CANTALAPIEDRA, Esther; HERNANDEZ HIGUERAS, Ana Isabel; VARELA BUSTO, Carmen; WO2011/36461; (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 1458-01-1 as follows. category: Pyrazines

The guanidine base was dissolved in anhydrousmethanol (2?3 mL/mmol) with methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (1 eq.) and refluxed for2 h under N2 atmosphere. The mixture was cooled toroom temperature, concentrated under reduced pressure,and purified by silica-gel column chromatography(Wako gel® C-200, 10percent methanol/chloroform) toafford series 3 (yield: 23?28percent). The spectral data of3a?3c were listed in the Supporting Information.

According to the analysis of related databases, 1458-01-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Murai, Masatoshi; Habu, Sayako; Murakami, Sonomi; Ito, Takeshi; Miyoshi, Hideto; Bioscience, Biotechnology and Biochemistry; vol. 79; 7; (2015); p. 1061 – 1066;,
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. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate

The guanidine base was dissolved in anhydrousmethanol (2?3 mL/mmol) with methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (1 eq.) and refluxed for2 h under N2 atmosphere. The mixture was cooled toroom temperature, concentrated under reduced pressure,and purified by silica-gel column chromatography(Wako gel® C-200, 10percent methanol/chloroform) toafford series 3 (yield: 23?28percent). The spectral data of3a?3c were listed in the Supporting Information.

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; Murai, Masatoshi; Habu, Sayako; Murakami, Sonomi; Ito, Takeshi; Miyoshi, Hideto; Bioscience, Biotechnology and Biochemistry; vol. 79; 7; (2015); p. 1061 – 1066;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem