Tag: M.W=100-200

56423-63-3, Adding a certain compound to certain chemical reactions, such as: 56423-63-3, name is 2-Bromopyrazine, 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 56423-63-3.

To a solution of Compound 18 (40 mg) in DMF (1.0 ml), NaH (5.2 mg, >55% in minerai oil) was added and after stirring for 30 minutes, 2-bromopyrazine (23.8 mg) was added and the mixture was stirred at room temperature for 0.5 hour. [0220] To the reaction mixture, DMSO (1.0 ml) was added and after filtering off the insoluble matter, the filtrate was purified by reverse-phase preparative HPLC to give the titled compound (6.7 mg, colorless oil.) 1H NMR (600MHz, CHLOROFORM-d) delta 8.34 – 8.29 (m, 1 H), 8.24 – 8.18 (m, 1 H), 8.13 – 8.08 (m, 1 H), 6.28 [6.19] (s, 1 H), 5.60 – 5.36 (m, 3 H), 4.24 – 4.13 (m, 1 H), 3.95 – 3.87 (m, 1 H), 3.82 – 3.69 (m, 1 H), 2.35 – 0.76 (m, 22 H)

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

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; ONO, Naoya; KURODA, Shoichi; SHIRASAKI, Yoshihisa; TAKAYAMA, Tetsuo; SEKIGUCHI, Yoshinori; USHIYAMA, Fumihito; OKA, Yusuke; EP2687524; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

19847-12-2, 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. 19847-12-2 name is Pyrazinecarbonitrile, 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.

Example 3 :f4aS RJaS)-7a-f2-fluoro-5-f2-fpyrazin-2-yl)-lH-imidazol-5-vDphenvn-5-methYl- 4a. .7.7a -t etrah ydro-4 H – f tiro Gamma3 ,4-d] f 1.3]thiazin-2-amineStep 1 : 2-(lH midazol-2-yl)py 2,2-Diethoxyethanamine (3 g, 2.25 mmol) was dissolved in dry methanol (20 mL). To this was added sodium methoxide (1.22 g, 22.5 mmol, as a 25% solution in methanol). After stirring for 25 minutes at room temperature,, pyrazine-2-carbonitrile (2.37 g, 22.5 mmol) and acetic acid (1.35 g, 22.5 mmol) were added and the subsequent solution was stirred at 50C for 1 hour. MeOH (40 mL) and 6N HC1 (12 mL) were added and the reaction was stirred at reflux overnight. The reaction mixture was cooled to room temperature and partitioned between 1 : 1 Et20 and water (60 mL) and the layers were separated. The aqueous layer was basified to pH 9/10 and extracted with 10% MeOH in DCM. The combined organic extracts were dried (MgSOa), filtered and concentrated to give the desired compound ( 1.49 g yellow solid). 1 H NMR (400 MHz, eOH-d,) delta ppm: 7.67 (s, 1 H), 7.09 (d, J=1.8 Hz, 1 H), 6.99 (d, J=2.5 Hz, 1 H), 5.72 (s, 2 H)

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

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD; DIMOPOULOS, Paschalis; HALL, Adrian; KITA, Yoichi; MADIN, Andrew; SHUKER, Nicola Louise; WO2012/93148; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

41110-33-2, 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 41110-33-2 as follows.

A solution of lithium aluminium hydride (164.0 mL, 0.164 mol, 1.0 M in THF, 0.5 equiv.) was added to a suspension of methyl 5-methylpyrazine-2-carboxylate (50 g, 0.328 mol, 1.0 equiv.) in anhydrous THF (750 mL) at -78 C (the internal temperature was kept below -72 C during addition of the lithium aluminium hydride). Upon completion of addition, the reaction mixture was stirred at -78 C for a further 20 mm and then quenched with glacial AcOH (50.0 mL) at the same temperature. The resulting mixture was warmed to RT and the volatiles were removed by evaporation under pressure. The residue was dissolved in 1.5 N HC1 (500 mL) and extracted with DCM (2 x 2 L). The organic layers were combined, washed with saturated aqueous NaHCO3 solution (2 x 500 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to yield the initial product as a brown oil. The residue was purified by column chromatography (silica gel 60-120 mesh) eluting with a gradient of 10% EtOAc in petroleum ether to provide the title compound as a pale yellow liquid (21.3 g, 53 %). 1H NMR (400 MHz, CDC13) oe 10.14 (s, 1H), 9.07 (d, J= 1.5 Hz, 1H), 8.63 (d, J= 1.4 Hz, 1H), 2.70 (s, 3H). LCMS (ESI positive ion) m/z:123 (M+H)t

According to the analysis of related databases, Methyl 5-methylpyrazine-2-carboxylate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common compound: 21948-70-9, name is 2-Methylthiopyrazine, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 21948-70-9

To a mixture of 2-(methylthio)pyrazine (59 mg, 0.46 mmol) and CuI (44.5 mg,0.23 mmol), MeCN (5 mL) was added and the suspension was stirred at ambient temperature for 1 h. The precipitated redorangepowder was centrifuged and re-crystallized from acetonitrile to give 36 mg (35%) of 1. FT-IR (KBr, cm-1): 376 (w),397 (w), 413 (w), 434 (w), 484 (m), 633 (w), 648 (w), 723 (m), 762 (vs), 964 (m), 1007 (m), 1053 (m), 1094 (m), 1130 (m),1159 (s), 1263 (m), 1375 (m), 1420 (s), 1456 (s), 1560 (m), 1584 (s), 2922 (w), 2963 (w), 2982 (w), 3061 (w), 3098 (w).Anal. Calcd (%) for C20H24Cu2I2N8S4: 27.1, 2.7, N 12.6, S 14.5. Found: 27.0, 2.9, N 12.5, S 14.7.

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, 21948-70-9, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Artem?ev; Beresin; Bagryanskaya, I. Yu.; Journal of Structural Chemistry; vol. 60; 6; (2019); p. 967 – 971; Zh. Strukt. Kim.; vol. 60; 6; (2019); p. 1008 – 1012,5;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 313339-92-3 name is 3,5-Dichloropyrazine-2-carbonitrile, 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. 313339-92-3

3,5-dichloropyrazine-2-carbonitrile (500 mg, 2.9 mmol), tert-butyl (R)-2-methylpiperazine-1-carboxylate (460 mg, 2.3 mmol), and K2CO3 (794 mg, 5.75 mmol) were combined in a 40 mLpressure vial. DMF (28 mL) was added and the reaction mixture was allowed to stir at rtovernight. The reaction mixture was then diluted with 3:1 chloroform/IPA (isopropyl alcohol)and washed with saturated, aqueous NH4Cl. The combined organic layers were washed withbrine, dried over magnesium sulfate (MgSO4), and concentrated in vacuo while loading ontosilica gel. The residue was purified by column chromatography (silica gel, eluting with agradient of 0-50% 3:1 EtOAc/EtOH in hexanes to afford tert-butyl (R)-4-(6-chloro-5-cyanopyrazin-2-yl)-2-methylpiperazine-1-carboxylate (I-1, 1.11 g, 3.29 mmol, 114 % yield), which needed to be dried further on the genevac to afford a pale yellow solid. MS (ESI) Calc?dfor (C15H21ClN5O2) [M+H]+, 338; found, 338.

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

Reference:
Article; Achab, Abdelghani; Augustin, Martin A.; Bass, Alan; Chen, Dapeng; Christopher, Matthew; Fradera, Xavier; Goldenblatt, Peter; Katz, Jason D.; Lampe, John; Lesburg, Charles A.; Li, Chaomin; Lipford, Kathryn; McGowan, Meredeth A.; Methot, Joey L.; Schroeder, Gottfried; Shaffer, Lynsey; Shah, Sanjiv; Witter, David; Zeng, Haoyu; Zhou, Hua; Bioorganic and medicinal chemistry letters; vol. 30; 1; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

50866-30-3, Name is 5-Methylpyrazine-2-carbaldehyde, 50866-30-3, 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.

The compound (82.2 mg) obtained in Example 47-3 was dissolved in methanol (5.0 ml) and added with the compound (35.9 mg) obtained in Example 73-1, followed by the addition of sodium cyanoborohydride (36.9 mg). Then, the reaction solution was adjusted to about pH 5 with acetic acid, followed by stirring at room temperature for 16 hours. The reaction solution was added with a saturated aqueous sodium bicarbonate solution and then extracted with chloroform. The organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off. The resulting crude product was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (84.0 mg) of the subject compound as a pale-yellow solid. MS(FAB,Pos.):m/z=526[M+H]+1H-NMR(500MHz,DMSO-d6):delta=0.87(6H,t,J=7.3Hz),1.69-1.78(4H,m),2.47(3H,s),2.86-2.95(4H,m),3.82(2H,s),3.85(2H,s),4.11(2H,s),4.26(2H,d,J=5.2H z),7.58-7.62(6H,m),7.88-7.89(2H,d,J=8.7Hz),7.95-7.96(2H,d,J=8.4Hz),8.47(1H,dd,J=0.6,1.3Hz),8.69(1H,d,J=1.4Hz ),10.47(1H,s),10.70(1H,brs),14.51(1H,brs).

Statistics shows that 5-Methylpyrazine-2-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 50866-30-3.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

109838-85-9,Some common heterocyclic compound, 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, molecular formula is C9H16N2O2, 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.

To a dry-ice / acetone cooled solution of scheme 5-8 compound S5 (5 g, 0.027 mol) in THF (50 ml), was added n-BuLi (2.5 M, 14.1 mL, 0.035 mol) dropwise for 30 mm. After addition, the reaction was stirred at this temperature for 30 mm, followed by dropwise addition of a solution of scheme 5-8 compound S4 (13.6 g, 0.04 mol) in THF (20 mL). The reaction mixture was stirred at this temperature for another 30 mm and allowed to stir at room temperature for 16 h. Then the reaction was quenched with aq. NH4C1 (50 mL) and extracted with ethyl acetate (60 mL x 2). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and then concentrated. The residue was purified by column chromatography on silica gel (eluted with petroleum ether: ethyl acetate =10:1) to give the title compound (6 g, yield 50.4%) and scheme 5-8 compound S4 (4.8 g) was recovered.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason Allan; PHADKE, Avinash S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (358 pag.)WO2017/35411; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

313339-92-3, Adding some certain compound to certain chemical reactions, such as: 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, 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 313339-92-3.

To a solution of 3,5-dichloropyrazine-2-carbonitrile (1.00 g, 5.47 mmol) in DMF (10 mL) was added (R)-()-3-amino-1-Boc-piperidine (1.38 g, 6.9 mmol) and DIPEA (2.0 mL, 10.94 mmol) in a dropwise manner. The mixture was stirred at room temperature for 60 min. The reaction mixture was evaporated under reduced pressure and the residue was purified by flash chromatography with 0 to 50% ethyl acetate in cyclohexane to give tert-butyl (3R)-3-[(6-chloro- 5-cyanopyrazin-2-yl)amino]piperidine-1-carboxylate (2.36 g, quantitative yield).

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 313339-92-3.

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
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. 59303-10-5, name is 2-Chloro-5-methylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. 59303-10-5

A solution of rac- I -((2S,3R,4R)-4-am ino-2-cyclopropyl-3-methyl-6-morpholino-3,4-dihydroqu inolin1(2H)-yl)ethanone (for a preparation see Intermediate 83, 100 mg, 0.304 mmol), DavePhos (11.95mg, 0.030 mmol), 2-chloro-5-methylpyrazine (46.8 mg, 0.364 mmol), Pd2(dba)3 (13.90 mg, 0.015 mmol) and sodium tert-butoxide (58.3 mg, 0.607 mmol) in 1,4-dioxane (3 mL) was stirred under nitrogen at 90 C for 20 h. The reaction mixture was allowed to cool to rt, filtered through celite and rinsed with ethyl acetate. The solvent was evaporated in vacuo then the sample was dissolved in 1:1 MeOH:DMSO (1 mL) and purified by MDAP (HpH). The appropriate fractions were combined andconcentrated in vacuo to give the title compound (36 mg, 0.085 mmol, 28%). LCMS (2 mm Formic): Rt = 0.84 mi [MH] = 422.

The synthetic route of 59303-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., 55557-52-3

The starting compound 3-chloropyrazine-2-carboxamide was synthesized using two published procedures. The first method was classified as less effective and was based on the homolytic amidation of 2-chloropyrazine. Thus, 2-chloropyrazine (0.17 mol) was dissolved in formamide (3.7 mol), heated to 90 C and ammonium peroxodisulphate (0.18 mol) was added portionwise over one hour period. This mixture reacted for another one hour at 90 C and then it was left to stand for 24 h at laboratory temperature. Dilution with 100 mL of water was followed by filtration and this filtrate was extracted continuously with chloroform for 16 h [34,42]. The mixture of three positional isomers was separated by flash chromatography using silica gel as stationary phase. The second process used 3-chloropyrazine-2-carbonitrile, which was submitted to partial hydrolysis of the nitrile group. The powdered carbonitrile (0.104 mol) was added little by little into the reaction mixture of concentrated hydrogen peroxide (0.95 mol) and water (195 mL) heated to 50 C. The pH was adjusted and regulated around a value of 9 using an 8% solution of sodium hydroxide and the temperature of the reaction was regulated between 55 and 60 C. The reaction was stopped after 2.5 h and was cooled to 5 C. Newly-emerged crystals were removed by suction and recrystallized from ethanol [42].

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; Jandourek, Ondrej; Dolezal, Martin; Kunes, Jiri; Kubicek, Vladimir; Paterova, Pavla; Pesko, Matus; Buchta, Vladimir; Kralova, Katarina; Zitko, Jan; Molecules; vol. 19; 7; (2014); p. 9318 – 9338;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem