Tag: M.W=100-200

Related Products of 1111638-10-8, 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. 1111638-10-8, name is 3-Chloro-5H-pyrrolo[2,3-b]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(1) To a solution of 3-chloro-5H-pyrrolo[2,3-b]pyrazin (4.69 g) in N,N-dimethylformamide (70 mL) were added potassium hydroxide (6.85 g) and iodine (15.5 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hours. Under ice-cooling, an aqueous sodium thiosulfate solution and ethyl acetate were added mm and after mixing, a solid is then filtrate to give 2 (3.96 g). The organic layer of the filtrate was separated, and the organic layer was sequentially washed with water and saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure to give 3-chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazin (4.29 g). APCI-MS m/z: 280/282 [M+H]+.

The synthetic route of 3-Chloro-5H-pyrrolo[2,3-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Pharmaceuticals Holding CO., LTD.; MITSUBISHI TANABE PHARMA CORPORATION; Iijima, Toru; Takahashi, Yoichi; Hirai, Miki; Sugama, Hiroshi; Togashi, Yuko; Shen, Jingkang; Xia, Guangxin; Wan, Huixin; US2015/232459; (2015); 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. 54608-52-5, name is 2-Hydrazinopyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C4H6N4

To a solution of 2-hydrazinylpyrazine (0.485 g, 4.40 mmol) in HOAc (6 mL) was added (2-(hydroxyimino)-l- phenylbutane-l,3-dione (0.765 g, 4.00 mmol) in small portions over 2 minutes. The mixture was stirred for 5 minutes and the resulting light orange suspension was stirred at 60 C for 6 hours. EtOH (1 mL) was added and the mixture was heated at 60 C for an additional 6 hours. The resulting dark green suspension was cooled to ambient temperature and the mixture was diluted with H20 (30 mL). The green suspension was stirred for 1 hour and the solid was collected via vacuum filtration. The collected solid was washed with H20 and dried in vacuum. The solid was suspended in EtOH (25 mL) and concentrated HC1 (500 muEpsilon) was added. The mixture was heated at reflux for 20 hours, cooled to ambient temperature and diluted with chilled H20 (75 mL). The mixture was treated with 1M NaOH to pH=7 and was extracted with Et20 (3X). The combined extracts were washed with saturated NaCl and dried over MgS04. The dried solution was filtered through packed Celite and concentrated. The residual green- yellow solid was purified on a Si02 column using step gradient elution (25% CH2C12, 50% EtOAc/hexanes) to furnish the title compound as a turquoise solid (325 mg, 31%). MS (apci) m/z = 266.1 (M+H).

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; ANDREWS, Steven, Wade; BLAKE, James, F.; BRANDHUBER, Barbara, J.; HAAS, Julia; JIANG, Yutong; KERCHER, Timothy; KOLAKOWSKI, Gabrielle, R.; THOMAS, Allen, A.; WINSKI, Shannon, L.; WO2014/78454; (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. 19847-12-2, name is Pyrazinecarbonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of Pyrazinecarbonitrile

Step 1 : To a mixture pyrazine-2-carbonitrile (2.0 g, 19.0 mmol) and 2-mercapto-propionic acid (2.1 g, 19.04 mmol) was added pyridine (3.0 mL, 38.1 mmol) and the mixture was heated to 100C for 2 h. The mixture was cooled to rt and EtOH (100 mL) was added and the RM was stirred at rt for 30 min. The formed precipitate was isolated though filtration and was washed with hex and was dried under reduced pressure to yield the desired compound (3.0 g, 15.5 mmol, 81 %). LC-MS (method 3): mlz [M+H]+ = 194.0 (MW calc. = 193.23); R, = 2.42 min.

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; GRUeNENTHAL GMBH; VOSS, Felix; RITTER, Stefanie; NORDHOFF, Sonja; WACHTEN, Sebastian; OBERBOeRSCH, Stefan; KLESS, Achim; WO2015/22073; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 21948-70-9, 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. 21948-70-9, name is 2-Methylthiopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Example 41Preparation of Compound 215Step A – Synthesis of 2-BenzylpyrazineTo a solution of 2-methylsulfanyl-pyrazine (1.26 g, 10 mmol) in 15 mL THF was added benzylzinc bromide (0.5M in THF, 40 mL, 20 mmol) followed by Pd(Ph3P)4 (1.16 g, 1 mmol). The resulting reaction was heated to 60 C and allowed to stir at this temperature for 2 hours, after which time the reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organic fraction was dried (sodium sulfate), filtered, and concentrated in vacuo to provide a crude residue which was purified using flash column chromatography (15% ethyl acetate in hexane) to provide 2- benzylpyrazine (0.76 g, 45% yield).

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

Reference:
Patent; SCHERING CORPORATION; WO2008/130581; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, 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. SDS of cas: 55557-52-3

Step 1: Into a 2000 mL 4 necked round bottom flask purged and maintained with an inert atmosphere of nitrogen were placed a solution of 3-chloropyrazine-2-carbonitrile (100 g, 716 mmol) in ethanol (660 mL), ethyl 2-sulfanylacetate (112 g, 932 mmol) and sodium carbonate (99 g, 930 mmol). The resulting solution was stirred for 4.5 h at 100 C in an oil bath. The reaction mixture was cooled to room temperature and poured into 7.5 L of water. The solid was collected by filtration. The solid was dissolved in 1500 mL of ethyl ether and filtered. The filtrate was concentrated under reduced pressure. This resulted in ethyl 7-aminothieno[2,3-Z>]pyrazine-6- carboxylate as a solid.

The synthetic route of 55557-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; GIBEAU, Craig, R.; (84 pag.)WO2016/144849; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 486460-20-2, A common heterocyclic compound, 486460-20-2, name is 3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine, molecular formula is C6H3F3N4, 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 5.0 g (26.6 mmol) of 3- (trifluoromethyl) -1,2,4-triazolo [4,3-a] pyrazine 3.0 g and a mass fraction of5% by weight of palladium on charcoal was charged into a 100 ml three-necked flask containing 50 ml of absolute ethanol and hydrogen gas was bubbled at 30 C under magnetic stirring,Atmospheric hydrogenation 20H, after the reaction is filtered, the filtrate by activated carbon decolorization, the column chromatography, yellow-brown liquid 3.5G, the yield 68.5%.

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; Nankai University; Wang, Baolei; Li, Zhengming; Zhang, Yan; (13 pag.)CN106749262; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 41270-62-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 41270-62-6 name is 2-Chloro-6-phenylpyrazine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: The Miyaura borylation reactions were carried out as follows: Chloropyrazines (3.0 mmol), B2pin2 (838 mg, 3.3 mmol), Pd(OAc)2 (14 mg, 2 mol %), PCy3 (34 mg, 4 mol %) and AcOK (750 mg, 7.5 mmol) was added in a 50 ml three necked flask fitted with a condenser, and dioxane (15 ml) was added at last. Then the reaction mixture was stirred at a preheated oil bath 110 oC under nitrogen atmosphere for 10 min. After complete completion of starting material checked by TLC, the reaction was cooled to room temperature, EtOAc (20 ml) was added. After filtration through Celite and concentration under vacuo, the resulting residue was precipitated from n-hexane:Et2O to afford corresponding boronic esters.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-6-phenylpyrazine, and friends who are interested can also refer to it.

Reference:
Article; Lu, Hongtao; Wang, Shengqiang; Li, Jingya; Zou, Dapeng; Wu, Yusheng; Wu, Yangjie; Tetrahedron Letters; vol. 58; 9; (2017); p. 839 – 842;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 16298-03-6,Some common heterocyclic compound, 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, molecular formula is C6H7N3O2, 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.

Methyl 3-aminopyrazine-2-carboxylate (100 g, 653.0 mmol) and N- bromosuccinimide (1 16.2 g, 653.0 mmol) were stirred in MeCN (1.198 L) at ambient temperature for 15 hours. The resultant precipitate was isolated by filtration and washed with MeCN (10 mL) and diethyl ether (100 mL) to give the sub-title product as pale yellow flakes (123.73g, 82% Yield). 1H NMR (400.0 MHz, CDCl3) delta 4.00 (s, 3H), 6.47 (br s, 2H), 7.28 (s, 1H) and 8.31 (s, 1H) ppm; (ES+) 232.0.

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; YOUNG, Stephen, Clinton; STORCK, Pierre-Henri; VIRANI, Aniza, Nizarali; REAPER, Philip, Michael; PINDER, Joanne; WO2011/143423; (2011); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 14508-49-7, 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. 14508-49-7, name is 2-Chloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

20.0 g (174.6 mmol) 2-chloropyrazine are added dropwise to 60.0 ml (61.7 g, 1.2 mol) hydrazine hydrate. The mixture is stirred at a bath temperature of 120 C. for 45 min. For working up, the cooled reaction mixture is left to stand at 2 C. for 12 h, the crystals which have precipitated out are filtered off and the residue on the filter is washed twice with petroleum ether. The residue is then recrystallized from toluene.Yield: 6.5 g (34% of th.)LC-MS (Method 1): Rt=0.49 min; MS (ESIpos): m/z=111 [M+H]+;1H-NMR (400 MHz, DMSO-d6): delta=8.11 (s, 1H), 7.94 (s, 1H), 7.90 (s, 1H), 7.70 (d, 1H), 4.29 (br. s, 2H).

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

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/305085; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 93049-39-9,Some common heterocyclic compound, 93049-39-9, name is 7-Chloropyrido[3,4-b]pyrazine, molecular formula is C7H4ClN3, 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.

EXAMPLE 417- [3 -(Piperidin- 1 -ylmethv0phenyl1pyrido[3 ,4-61pyrazine4,5-Diamino-2-chloropyridine (35 mg, 0.24 mmol) was dissolved in ethanol (1 mL) and glyoxal (0.5 niL, 40% in water) was added. After standing for 18 h the mixture was partitioned between water and EtOAc (20 mL each). The organic phase was washed with water, dried (MgSO4) and concentrated in vacuo. The residue was dissolved in DME (0.7 mL), and 3-(piperidin-l-ylmethyl)phenylboronic acid pinacol ester hydrochloride (81 mg, 0.24 mmol), 2M aqueous sodium carbonate solution (0.35 mL, 0.7 mmol) and Pd(PPh3)4 (8 mg, 0.007 mmol) were added. The mixture was heated to 12O0C in a sealed tube, under microwave irradiation, for 20 minutes. After cooling, the mixture was partitioned between water and EtOAc (2 mL each). The organic phase was concentrated in vacuo and the residue was purified by preparative HPLC to give the title compound (53 mg, 64%) as a pale yellow gum. deltaH (CDCl3) 9.63 (d, IH), 9.03 (d, IH), 8.92 (d, IH), 8.37 (d, IH), 8.17 (s, IH), 8.08-8.14 (m, IH), 7.44-7.57 (m, 2H), 3.74 (s, 2H), 2.50-2.65 (m, 4H), 1.59-1.73 (m, 4H), 1.40-1.54 (m, 2H). LCMS (ES+) 305 (M+H)+, RT 1.89 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Chloropyrido[3,4-b]pyrazine, its application will become more common.

Reference:
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem