Tag: M.W=200-300

The chemical industry reduces the impact on the environment during synthesis 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, I believe this compound will play a more active role in future production and life. 87486-34-8

A flask equipped with a magnetic stirrer was charged with l-(2-(tert- butyldimethylsilyloxy)ethyl)-lH-pyrazol-4-amine 116b (1. 7 g, 7.1 mmol), 3,5-dibromo-l- methylpyrazin-2(lH)-one (1.25 g, 4.7 mmol), and IPA (25 rriL). The system was evacuated and then refilled with N2. The reaction mixture was heated at 90¡ãC for 6 h. Then, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash column chromatography eluting with petroleum ether/ethyl acetate to afford 140a (1.7 g, 78percent). LCMS: [M+H]+ 314.

The chemical industry reduces the impact on the environment during synthesis 87486-34-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (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 951626-95-2 as follows. 951626-95-2

To the solution of piperidine (25 mg, 0.29 mmol) in dry THF (5 mL) was added trimethylaluminium (0.14mL, 0.29 mmol) drop wise at -10C under nitrogen over a period of 10 min. This solution was allowed to stir at room temperature for 45 minutes. Further the reaction mixture was re-cooled to -10C and thereto was added a solution of compound 5a (50 mg, 0.22 mmol) in THF (2.5 mL) drop wise. The resulting reaction mixture was stirred at room temperature initially then refluxed for 18 h. Reaction mixture was cooled to room temperature and quenched with iso-propanol (IPA) followed by methanol and then with saturated Na2SO4 solution. The reaction mixture was filtered and the filtrate was evaporated to dryness. The crude material was purified by column chromatography on silica gel (100-200 mesh) using MeOH in DCM to give desired compound 6a (50 mg, 85%). MS (ES+) m/z: 249. 1H NMR (400 MHz, CDCl3) delta 7.13 (s, 1H), 6.14-6.28 (m, 1H), 4.43 (m, 2H), 3.77-3.85 (m, 2H), 3.68-3.74 (m, 4H), 1.51-1.76 (m, 6H)

According to the analysis of related databases, 951626-95-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Surase, Yogesh B.; Samby, Kirandeep; Amale, Sagar R.; Sood, Ruchi; Purnapatre, Kedar P.; Pareek, Pawan K.; Das, Biswajit; Nanda, Kamna; Kumar, Subodh; Verma, Ashwani K.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3454 – 3459;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

313340-08-8, A common heterocyclic compound, 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, molecular formula is C7H7Cl2N3O, 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.

Compound6(10 mmol) was dissolved in 2N HCl/MeOH (15 ml) solution. The mixture was stirred at 70oC for 7 h. The solution was concentrated under vacuum, diluted with saturated NaHCO3(60 ml) and then extracted with CH2Cl2(3¡Á80 ml). The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product7aslight yellowsolid in 81% yield.

The synthetic route of 3,5-Dichloro-6-ethylpyrazine-2-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yueliang; Xing, Li; Ji, Yinchun; Ye, Jiqing; Dai, Yang; Gu, Wangting; Ai, Jing; Song, Zilan; Bioorganic and Medicinal Chemistry Letters; vol. 29; 6; (2019); p. 836 – 838;,
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21943-17-9,Some common heterocyclic compound, 21943-17-9, name is 5-Bromo-3-chloropyrazin-2(1H)-one, molecular formula is C4H2BrClN2O, 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.

General procedure: A solution of 56 (1.50 g, 7.16 mmol), the appropriate secondary amine (8.59 mmol, 1.20 equiv) and diisopropylethylamine (1.50 mL, 8.59 mmol) in n-butanol (15 mL)was heated in a microwave reactor using variable wattage to 140 C for 1 h. The mixture was concentrated and purified by flash column chromatography on silica, eluting with 9:1 dichloromethane/methanol, to give gave 58-63.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-3-chloropyrazin-2(1H)-one, its application will become more common.

Reference:
Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728,16;; ; Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728;,
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117719-17-2, The chemical industry reduces the impact on the environment during synthesis 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, I believe this compound will play a more active role in future production and life.

To a solution of Intermediate 1-02 (3 g, 9.288 mmol) in 2-propanol (46 mL), 2- chloro-3-oxo-succinic acid diethyl ester (6.2 g, 27.865 mmol) was added. The reaction mixture was heated in a Parr reaction vessel at 90 C for 2 days. The solvent was evaporated and the residue was purified by automated column chromatography (Biotage, EtOAc:Cyclohexane, 0: 100 to 40:60). The product obtained was treated with Et20 and filtered to give the expected product 1-39 (1.2 g, 34 %) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-3-morpholinopyrazin-2-amine. I believe this compound will play a more active role in future production and life.

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,
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These common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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. 24241-18-7

5-Bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine 2 [00178] (Trimethylsilyl)acetylene (1.845 g, 2.655 mL, 18.78 mmol) was added dropwise to a solution of 3,5-dibromopyrazin-2-amine 1 (5 g, 19.77 mmol) in DMF (25 mL) Triethylamine (10.00 g, 13.77 mL, 98.85 mmol), copper(I) iodide (451.7 mg, 2.372 mmol) and Pd(PPh3)4 (1.142 g, 0.9885 mmol) were then added and the resulting solution stirred at RT for 30 minutes. The reaction mixture was diluted with EtOAc and water and the layers separated. The aqueous layer was extracted further with EtOAc and the combined organic layers washed with water, dried (MgS04) and concentrated in vacuo. The residue was purified by column chromatography eluting with 15% EtO Ac/Petroleum ether to give the product as a yellow solid (3.99g, 75% Yield). 1H NMR (400.0 MHz, DMSO) d 0.30 (9H, s), 8.06 (IH, s); MS (ES+) 271.82

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 24241-18-7.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; YOUNG, Stephen, Clinton; DAVIS, Christopher, John; STUDLEY, John; WO2013/49719; (2013); A1;,
Pyrazine – Wikipedia,
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A common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, molecular formula is C4H3Br2N3, 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. 24241-18-7.

Making reference to Scheme 5, to a solution of 3,5-dibromopyrazin-2-amine (10 g, 40 mmol), copper(I) iodide (0.91 g, 4.7 mmol), diisopropylethylamine (53 mL, 0.55 mol), and tetrakis(triphenylphosphine)-palladium(0) (2.3 g, 1.9 mmol) in DMF (120 mL) that was de-gassed with Ar was added trimethylsilylacetylene (6.7 mL, 48 mmol). The resulting mixture was stirred under an Ar atmosphere for 1 h at 120C, after which it was evaporated to dryness in vacuo. The residue was subjected to silica gel chromatography eluting with 35% EtOAc in hexanes to give a brown oil that was triturated with hexanes to give the title compound (5.0 g, 47%). XH NMR (CDC13, 300 MHz): delta 8.04 (s, 1H), 5.10 (s, 2 H), 0.28 (s, 9H). HPLC retention time: 2.75 minutes. MS ESI (m/z): 270.0, 272.0 (M+H)+, calc. 269

The synthetic route of 2-Amino-3,5-dibromopyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF ROCHESTER; BOARD OF REGENTS OF THE UNIVERSITY OF NEBRASKA; GELBARD, Harris A.; DEWHURST, Stephen; GENDELMAN, Howard E.; WO2014/85795; (2014); A1;,
Pyrazine – Wikipedia,
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A common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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. 63744-22-9.

To 4-(4-(oxetan-3-yl)piperazin-l-yl)aniline II (2.00 g, 8.57 mmoles), Hunig’s base (3.29 mL) and 6,8-dibromoimidazo[l,2-a]pyrazine (2.37 g, 8.57 mmoles) was added in DMF (43 mL). The reaction was stirred at 85 C in a pressure tube for overnight. The material was quenched with saturated sodium bicarbonate, extracted with DCM (120 mL x 3) and the organic layers were combined and washed with water (120 mL x 3), dried over anhydrous sodium carbonate and concentrated. The crude material was purified using a 120 g Isco column and eluted off using a stepwise gradient of 0-60% (10% MeOH/DCM). The desired fractions were combined and concentrated to provide the title compound III.

The synthetic route of 6,8-Dibromoimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; DI PAOLO, Julie, A.; LIN, Joseph, Haw-Ling; LIN, Shao-Lee; (86 pag.)WO2016/172117; (2016); A1;,
Pyrazine – Wikipedia,
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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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, A new synthetic method of this compound is introduced below., 24241-18-7

Magnesium turnings (293.9mg, 12.1mmol, 3.0equiv) and I2 (153.6mg, 605mumol, 0.15equiv) were added to a dry 100-mL 2-necked round-bottom flask under an argon atmosphere. Freshly distilled THF (25mL) was added using a syringe. The mixture was stirred at 0¡ãC until the brown color of the I2 disappeared. Then, benzylbromide (1.44mL, 12.1mmol, 3.0equiv) was slowly added using a syringe. After 10min ZnCl2 was added and the mixture was stirred for 40min. To this mixture, bis(triphenylphosphine)palladium (II) dichloride (141.8mg, 0.20mmol, 0.05equiv) and a solution of 2-amino-3,5-dibromopyrazine (1.02g, 4.03mmol, 1.0equiv) in dry THF (25mL) were added sequentially at room temperature. The resulting orange-colored reaction mixture was stirred for 3 days at room temperature and then quenched with water (50mL) at 0¡ãC. The mixture was diluted with ethyl acetate (300mL) and water (100mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (4¡Á200mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated on a rotary evaporator. The residue was dissolved in CH2Cl2 and purified by silica gel column chromatography (gradient elution: PE?EtOAc, 85:15?65:35) to afford compound 11 (738.2mg, 2.79mmol, 70percent) as viscous yellow oil. Rf=0.46 (silica gel, PE?EtOAc, 7:3); 1H NMR (400MHz, CDCl3): delta=7.93 (s, 1H), 7.26?7.21 (m, 2H), 7.20?7.15 (m, 1H), 7.15?7.10 (m, 2H), 4.40 (br s, 2H), 3.99 (s, 2H); 13C NMR (100MHz, CDCl3): delta=152.3, 142.6, 141.9, 135.8, 129.2, 128.6, 127.4, 126.4, 40.9; IR (neat): numax=3472, 3314, 3200, 3060, 3027, 2919, 2850, 1605, 1555, 1529, 1494, 1424, 1389, 1340, 1261, 1220, 1158, 1117, 1073, 1048, 1028, 1002, 923, 905, 791, 759, 726, 696, 634cm?1; HRMS (ESI): calcd for C11H1179BrN3+ 264.0131; found 264.0133; calcd for C11H1181BrN3+ 266.1414; found 266.0113. The spectroscopic data are in good agreement with those reported in the literature.11d

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; Vece, Vito; Vuocolo, Giuseppina; Tetrahedron; vol. 71; 46; (2015); p. 8781 – 8785;,
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. 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. 1458-01-1

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.

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

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