Month: July 2021

Electric Literature of 24241-18-7,Some common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, molecular formula is C4H3Br2N3, 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-(ii): Synthesis of 6, 8-dibromoimidazo [1, 2-a] pyrazine:To a stirred solution of Intermediate-lOa (0.2 g, 0.79 mmol) in IPA (5niL) was added Chloro acetaldehyde (0.12 mL, 0.952 mmol), and stirred at 100C for 24h. After the reaction was completed, the reaction mixture was cooled RT, pale brown solid was precipitated out, filtered the solid dried under vaccum to get the desired product (150 mg, 53%); 1H NMR (400 MHz, DMSO-d6): oe 9.02(s, 1H), 8.24(s, 1H), 7.9(s, 1H); MS (ES) m/z 277.9 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-3,5-dibromopyrazine, its application will become more common.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BORUAH, Anima; HOSAHALLI, Subramanya; PANIGRAHI, Sunil Kumar; WO2014/125410; (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. 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

Synthetic Route of 59489-71-3,Some common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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.

Sodium nitrite (1. 35 g, 19. 53 MMOL) was added portionwise to concentrated sulfuric acid (9. 8 mL) at 0 C. The mixture was heated at 50 C until all of the sodium nitrite had dissolved and the mixture was again cooled to 0 C. A solution of 5- BROMO-PYRAZIN-2-YLAMINE (2. 57 g, 14. 68 MMOL) in concentrated sulfuric acid (14. 7 mL) was added dropwise to the nitronium solution at 0 C. The ice bath was removed, the mixture warmed to ambient temperature and stirred for 15 minutes before heating to 45 C for seven minutes. After cooling to ambient temperature, the mixture was poured slowly with precaution into crushed ice water (100 mL). The aqueous phase was neutralized to pH 4 with 20% aqueous sodium hydroxide then extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were washed with water (50 mL), dried (anhydrous magnesium sulfate), filtered, and evaporated to afford the title compound (1. 88 g, 73%) as a yellow solid. ‘H NMR (CDCl3, 300 MHz) ; 8. 07 (1 H, s), 7. 62 (1 H, D, J = 3. 0 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-bromopyrazine, its application will become more common.

Reference:
Patent; PFIZER INC.; WO2004/92145; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 27825-21-4, The chemical industry reduces the impact on the environment during synthesis 27825-21-4, name is Methyl 3-chloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

The mixture of 1.35 g (7.8 mmol, 1 eq.) of 3-chloro-2-pyrazine methyl carboxylate prepared in example 20a), 0.7 ml (7.8 mmol, 1 eq.) of methyl thioglycolate and 1.62 g (11.7 mmol, 1.5 eq.) of K2CO3 in 60 ml of acetonitrile is heated under stirring for 16 hrs. The solvent is concentrated and immersed in 200 ml of water. After acidifying with 1N HCl, extraction is performed 3 times with CH2Cl2, the organic phase is dried on Na2CO3, filtered and evaporated. 1.21 g (73.5%) of aromatized product is obtained. FP=188 C. NMR (1H, DMSO): 2.50 (s; 3H; SCH3), 3.87 (s; OCH3), 8.81 (d, J=2.3 Hz; 1H, arom. H), 8.86 (d, J=2.3 Hz; 1H; arom. H), 11.67 (m; 1H; OH).

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

Reference:
Patent; Imbert, Thierry; Monse, Barbara; Koek, Wouter; US2005/80085; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 75907-74-3, These common heterocyclic compound, 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, 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 (1): to a 50 ml three-necked flask, the QR01006-IN-01 (500 mg, 3.29 mmol), dichloromethane (10 mL), chloromethyl chloroformate (460 mg, 3.6 mmol) were added. The resultant mixture solution was controlled at the temperature of -2 C., and then pyridine (0.32 mL) was dropwise added while controlling the temperature of no greater than 3 C. After the dropwise addition, the reaction solution was heated to room temperature and stirred overnight. The TLC (petroleum ether/ethyl acetate=1:3) was used to monitor the reaction until the raw materials were fully reacted. The reaction solution was filtered, and the resulting filtrate was dried by rotary evaporation, to give 1.1 g of yellow oil. The yellow oil was purified by preparative plate to give 620 mg of yellow liquid, with the yield of 77.3%. LCMS and HNMR spectra can confirm the structure of the target compound.

Statistics shows that (3,5,6-Trimethylpyrazin-2-yl)methanol is playing an increasingly important role. we look forward to future research findings about 75907-74-3.

Reference:
Patent; WUHAN LL SCIENCE AND TECHNOLOGY DEVELOPMENT CO., LTD; WUHAN QR PHARMACEUTICALS CO., LTD; GE, Jian; MA, Jianyi; XIANG, Guangya; WANG, Wei; WANG, Chaodong; (46 pag.)US2017/22188; (2017); 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

These common heterocyclic compound, 33332-25-1, name is Methyl 5-chloropyrazine-2-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. Recommanded Product: 33332-25-1

Step 1: methyl 5-{3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl) ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}pyrazine-2-carboxylate (R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (0.065 g, 0.10 mmol) was added to a mixture of {3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dihydrochloride (0.50 g, 1.0 mmol), methyl 5-chloropyrazine-2-carboxylate (0.18 g, 1.0 mmol)(Ark Pharm, Inc., Cat. No.: AK-23920), and cesium carbonate (1.0 g, 3.1 mmol) in toluene (15.0 mL) under nitrogene, followed by palladium acetate (0.023 g, 0.10 mmol). The reaction mixture was stirred at 120 C. for 3 h. After cooled to r.t., the reaction mixture was filtered through a pad of celite, washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in dichloromethane (0-70%) to afford the desired product (0.31 g, 55%). LCMS (M+H)+: m/z=546.3.

The synthetic route of Methyl 5-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Vaddi, Krishna; US2015/246046; (2015); 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 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. 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2,3-Pyrazinecarboxylic anhydride

A mixture of 1 -ethyl-7-hydroxy-2,2,4-trimethyl- 1 ,2-dihydroquinoline (1.15 mmole), l-(5- carboxypentyl)-7-hydroxy-2,2,4-trimethyl-l,2-dihydroquinoline (1.15 mmole), 2,3- pyrazinedicarboxylic anhydride (1.15 mmole) and 50 mg p-toluenesulfonic acid is stirred in propionic acid (80 mL) at 140 C for 24 hours. The solvent is removed under vacuum and the product is purified by a silica gel column eluting with MeOH/CHCl3.

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

Reference:
Patent; BIOTIUM, INC.; MAO, Fei; LEUNG, Wai-Yee; CHEUNG, Ching-Ying; HOOVER, Hye Eun; WO2011/68569; (2011); A1;,
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