Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, 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 63744-22-9, Recommanded Product: 63744-22-9

Intermediate Example 2-1:Preparation of 6-bromo-8-methylsulfanyl-imidazo[1,2-a]pyrazineTo a stirred suspension of intermediate example 1-1 6,8-dibromo-imidazo[1,2-a]pyrazine (489 g, 1766 mmol) in MeOH (2900 mL) at -20 C was dropwise added a solution of sodium methan thiolate (225 g, 3214 mmol, 1.8 eq) in 800 mL water. After stirring overnight, the clear solution was poured on 30 L water and the yellowish precipitate was filtered, washed with 3 L water and dried in vaccuo to yield 301 g 6-bromo-8-methylsulfanyl-imidazo[1,2-a]pyrazine (69.8 %). 1H-NMR (300 MHz, d6-DMSO): delta = 8.64 (1H, s), 8.00 (1H, d), 7.66 (1H, d2.54 (3H, s) ppm.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80230; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-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 1458-01-1, COA of Formula: C6H7ClN4O2

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. 369638-68-6, name is tert-Butyl (5-methylpyrazin-2-yl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Safety of tert-Butyl (5-methylpyrazin-2-yl)carbamate

Intermediate: te/t-butyl 5-(bromomethyl)pyrazin-2-ylcarbamate (29b)BocHNgammaN.(29b)To a solution of te/t-butyl 5-methylpyrazin-2-ylcarbamate (29a) (100 g, 0.48 mol) inCCU (40 mL) was added NaHCO,? followed by AZ-bromosuccinimide (130 g, 0.57 mol). The resulting mixture was heated to reflux at 800C for 12 hours then cooled to room temperature. The reaction mixture was filtered through Cehte and the filtrate was concentrated in vacuo. The crude product was chromatographed (SiO?; 5 % EtOAc in CHCI3) to give tert-buty 5-{bromomethyi)pyrazm-2-y.carbamate (29b).

According to the analysis of related databases, 369638-68-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; BENBOW, John William; LOU, Jihong; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/13161; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 762240-92-6,Some common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, molecular formula is C6H8ClF3N4, 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 1: Preparation of tert-butyl (R)-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-alpha]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)-4-oxobutan-2-ylcarbamate (Compound of formula 2 wherein R is Boc) [35] (R)-3-Boc-amino-4-(2,4,5-trifluorophenyl)-butanoic acid (3.0g, 9.0mmol) and tetrahydrofuran (THF, 30ml) were charged and dissolved in a dry flask, and N-methylmorpholine (2.97ml, 27.0mmol) was added thereto. Then, the mixture was cooled to a temperature of 0 to 5C, and 2-chloro-4,6-dimethoxy-1,3,5-triazine (2.05g, 11.7mmol) was added thereto. After being stirred at a temperature of 0 to 5C for one hour, 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-alpha]pyrazine hydrochloride (2.47g, 10.8mmol) was added and the reaction mixture was stirred while elevating to a temperature of 20 to 25C. After the completion of the reaction was confirmed by TLC, the reaction liquid was cooled to 10C, and dichloromethane (30.0ml) and water (30.0ml) were added thereto, followed by separation of layers. The organic layer was washed with saturated sodium bicarbonate (30.0ml) and saline (30.0ml), dried over anhydrous sodium sulfate, concentrated under reduced pressure, and then crystallized from ethyl acetate (12.0ml) and isopropyl alcohol (6.0ml) to afford 4.29g (yield: 94.0%) of tert-butyl (R)-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-alpha]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)-4-oxobutan-2-ylcarbamate.[36] 1H NMR delta 7.04(dd, 1H, J=0.012), 6.84(dd, 1H, J=0.013), 5.01(s, 2H), 4.90(NH), 4.20(s, 2H), 4.10(t, 2H), 4.04(t, 2H), 3.97(m, 1H), 2.97(t, 2H), 2.70(t, 2H),[37] mp: 183.0 to 183.5C (as measured using a capillary melting point apparatus Mettler FP90 at an elevation rate of 2C/min)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, its application will become more common.

Reference:
Patent; ST PHARM CO., LTD.; LIM, Geun Gho; CHANG, Sun Ki; BYEON, Chang Ho; WO2012/99381; (2012); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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. Recommanded Product: 24241-18-7

A mixture of morpholine (50 mL) and 3,5-dibromo-2-aminopyrazine (12.50 g) was refluxed for 1 h until the reaction was complete by TLC analysis. The solution was cooled to room temperature andadded to a beaker containing ice water (300 mL) with continuous stirring. The solid was precipitated and filtered. After drying, 12.30 g of a yellow solid with a metallic luster was obtained (a yield of 96.1%). 1H-NMR (DMSO-d6) delta 7.70 (s, 1H), 6.28 (s, 2H), 3.85-3.62 (m, 4H), 3.04 (d, J = 4.0 Hz, 4H).

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Shan; Sun, Chengyu; Chen, Chen; Zheng, Pengwu; Zhou, Yong; Zhou, Hongying; Zhu, Wufu; Molecules; vol. 22; 2; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 330786-09-9, The chemical industry reduces the impact on the environment during synthesis 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

Step 3: ethyl 3,5-dimethoxypyrazine-2-carboxylate To a solution of methyl 3,5-dichloropyrazine-2-carboxylate (0.312 g, 1.51 mmol) in THF (4.5 mL) at room temperature was added sodium hydride (60% wt. dispersion, 0.199 g, 4.98 mmol) and methanol (0.200 mL, 4.94 mmol). The reaction mixture was stirred at room temperature for 30 min, diluted with EtOAc, and quenched with saturated NH4Cl. The reaction mixture was partitioned between brine and EtOAc. The aqueous phase was extracted with EtOAc (3*) and the combined organic extracts were washed with brine (1*), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (10% to 50% EtOAc in hexanes) gave ethyl 3,5-dimethoxypyrazine-2-carboxylate (0.314 g, 1.48 mmol, 98% yield) as an off white solid.

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

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 132426-19-8, name is 2-Bromo-1-(pyrazin-2-yl)ethanone, 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 132426-19-8, Recommanded Product: 132426-19-8

Step 1. 3-Amino-6-chloro-1-(ethoxycarbonyl)-2-(pyrazine-2-carbonyl)indole The title compound was prepared according to the procedure described in step 2 of Example 1 from 4-chloro-2-(ethoxycarbonylamino)benzonitrile (Example 1, step 1) and 2-(bromoacetyl)pyrazine (prepared according to the method of F. H. Case et al., J. Am.Chem.Soc., 1956, 78, 5842). 1H-NMR (CDCl3) delta: 9.26 (1H, d, J=1.5 Hz), 8.67 (1H, d, J=2.6 Hz), 8.56 (1H, dd, J=1.5, 2.6 Hz), 8.21 (1H, d, J=1.8 Hz), 7.55 (1H, d, J=8.4 Hz), 7.27 (1H, dd, J=1.5, 8.4 Hz), 6.18 (2H, br s), 3.87 (2H, q, J=7.0 Hz), 0.93 (3H, t, J=7.0 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-(pyrazin-2-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; US6300363; (2001); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, 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 63744-22-9, category: Pyrazines

[0310] 6-Bromo-N-(4-(4-(oxetan-3-ylmethyl)piperazin-1-yl)phenyl)imidazo[1,2- a]pyrazin-8-amine XXXI: To a seal tube equipped with a stirring bar, 4-(4-(oxetan-3- ylmefhyl)piperazin-1-yl)aniline XXX ( 1.19 g, 4.81 mmol), 6,8-dibromoimidazo[1,2- a]pyrazine (1.33 g, 4.81 mmol), isopropanol (24.1 mL), and diisopropylethylamine (1.37 g, 10.58 mmol) were added, and the reaction mixture was heated at 100 C overnight. Most solvents were removed in vacuo and DCM (200 mL) was added to the mixture. The solution was washed with H2O (20 mL x 2), brine (20 mL x 1), dried over Na2S04, filtered and solvents were removed in vacuo. The resulting residue was passed through a silica gel column (MeOH: DCM = 5: 95) and light red solids were obtained as the desired compound XXXI, 0.692 g (yield 32.4 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6,8-Dibromoimidazo[1,2-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; BLOMGREN, Peter, A.; CLARKE, Astrid; CURRIE, Kevin, S.; DI PAOLO, Julie; KROPF, Jeffrey, E.; LEE, Seung, H.; LO, Jennifer, R.; MITCHELL, Scott, A.; SCHMITT, Aaron, C.; SWAMINATHAN, Sundaramoorthi; XIONG, Jin-Ming; XU, Jianjun; ZHAO, Zhongdong; (169 pag.)WO2016/10809; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 944709-42-6, name is 6,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine, 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 944709-42-6, Recommanded Product: 944709-42-6

Into a flask, under an inert atmosphere of nitrogen, was placed 1,1,1-trifluoro-4-iodobutane (6.7 g, 28 mmol), zinc metal (3.7 g, 56 mmol) and DMA (10 mL). This was followed by the dropwise addition of a solution of iodine (0.33 g, 1.3 mmol) in DMA (0.5 mL). The resulting mixture was stirred for 3 h at 80¡ãC. The reaction was cooled and directly used in the next step. Into a flask, under an inert atmosphere of nitrogen, was placed 6,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (6.0 g, 22 mmol), Pd(PPh3)2Cl2 (0.91 g, 1.3 mmol) and THF (80 mL). The resulting mixture was allowed to stir for 1 h at RT. The intermediate from Step A (11 mL, 28 mmol) was added and the resulting solution was stirred for 16 h at RT. The reaction was quenched by the addition of sat. aq. NH4Cl. The resulting solution was extracted with EtOAc (3X) and the organic layers were combined, washed with brine, dried over anhydr. Na2SO4, and filtered. The filtrate was conc. in vacuo to dryness. The residue purified by silica gel chromatography with EtOAc:petroleum ether (0-20percent) to afford the title compound.

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, 6,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BERGER, Raphaelle; DONG, Guizhen; RAGHAVAN, Subharekha; YANG, Zhiqiang; (179 pag.)WO2017/200857; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 13301-04-7, A common heterocyclic compound, 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, molecular formula is C6H4Br2N2O2, 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.

To a dimethylformamide (15 ml) solution of 3,6-dibromopyrazine-2-carboxylic acid methyl ester (see Patent Document: BE662507)(780 mg, 2.64 mmol), potassium carbonate (364 mg, 2.64 mmol)) and 4-fluorothiophenol (0.253 ml, 2.37 mmol) were sequentially added at room temperature and the mixture was stirred at room temperature for one hour. The reaction solution was charged with water, extracted with chloroform and then dried (over anhydrous magnesium sulfate), filtered and concentrated to obtain a residue, which was purified by silica gel column chromatography [developing eluent: chloroform hexane = 1:2 to 10:0] and purified by recycle preparative HPLC (LC-908 type, Japan Analytical Industry Co. , Ltd.) [developing eluent: chloroform] to obtain a mixture of 6-bromo-3-[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester and 3-bromo-6-[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester (940 mg) in the form of a light yellow solid substance.

The synthetic route of 13301-04-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Nissan Chemical Industries, Ltd.; EP2157090; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem