Tag: M.W=300-400

Related Products of 1245644-42-1, These common heterocyclic compound, 1245644-42-1, name is 6-Bromo-3-iodoimidazo[1,2-a]pyrazine, 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 solution of 6-bromo-3-iodoimidazo[l ,2-a]pyrazine (3 g, 9.26 mmol) in DMF (50 mL), were added 4-cyanophenylboronic acid 3 (1.632 g, 11.1 mmol), K3P04 (4.91 g, 23.15 mmol), Pd(PPh3)4 (0.534 mg, 0.46 mmol) and water (5 mL). The reaction mixture was heated at 90 C for 1 h and water was added to the mixture to induce precipitation. The precipitate was isolated by filtration and was purified by column chromatography (silica gel, eluent petroleum ether/EtOAc 1 :1) to afford of 4-(6-bromoimidazo[l,2-a]pyrazin-3-yl)benzonitrile (2.5 g, 90%) as an off-white solid. 1H NMR (400 MHz, DMSO-< delta 9.88 (s, 1H), 8.90 (s, 1H), 8.27 (s, 1H), 8.05-7.99 (m, 4H); MS (ESI) m/z 301.1 [C13H7BrN4+2 ]+. The synthetic route of 1245644-42-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-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. category: Pyrazines

EXAMPLE 176; 7- {5- [(6,7-dichloro- 1-oxo- 1 ,2-dihydr opyr rolo [1 ,2-alphal pyrazin-4-yl)methyll -2- fluorobenzoyl}-3-pyrrolidin- l-yl-5,6,7,8-tetr ahydro [ 1 ,2,41 triazolo [4,3-alphal pyrazin-2-ium trifluoroacetate (AA2)Step 1: 3-Pyrrolidin-l-yl-5,6,7,8-tetrahydro[l,2,41triazolo[4,3-alphalpyrazin-7-ium trifluoroacetate (AAl)A mixture of tert-bvXy 3-bromo-5,6-dihydro[l,2,4]triazolo[4,3-alpha]pyrazine-7(8H)-carboxylate(0.231 mmol) in pyrrolidine (3 ml) was stirred overnight in a sealed tube at 6O0C. The volatiles were removed under reduced pressure and the resulting crude was diluted with DCM and washed with sat. aq. NH4Cl solution. The organic phase was dried (Na2SO4) and filtered. Evaporation of the solvent provided a crude which was dissolved in a mixture of DCM/TFA (1:1, 0.23 M) and stirred at room temperature for 30 min. The volatiles were removed under reduced pressure and the resulting crude was used as such in the next step without purification. MS (ES) C9H15N5 required: 193, found: 194 (M+H)+.

The synthetic route of tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2007/138355; (2007); 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. 243472-70-0, name is 5-Bromo-2,3-diphenylpyrazine, A new synthetic method of this compound is introduced below., Safety of 5-Bromo-2,3-diphenylpyrazine

To 50 g (0.161 mol) of 5-bromo-2,3-diphenylpyrazine, 116 g (0.884 mol, 5.5 eq/mol) of 4-(isopropylamino)-butan-1-ol and 13.33 g of KI (0.080 mol, 0.5 Eq/mol) were added. The reaction mixture was stirred, warmed and then heated up to 140C for about 18-20 hrs. The reaction was monitored by TLC up to completion (starting material about 1% by TLC). The reaction mixture was cooled down to room temperature. After the reaction was completed, the following work up step was performed: Option 1 : Ethyl acetate was added (500 mL, 10 vol) and the organic phase was washed with water (150 mL, 3 vol). The organic phase was separated and aqueous phase was extracted with ethyl acetate (150 mL, 3 vol). The organic phases were joined and washed with water (200 mL, 2 vol) three times. The solvent was distilled off under vacuum at not more than (“NMT”) 40C until 1 vol (oil appearance). Option 2: The material (reaction mixture obtained in step a) was dissolved in acetone (250 mL, 5vol), the solution obtained was cooled down to 0C to 5C and anti-solvent / water was added (1000 mL, 20 vol) for 40 minutes, then the suspension was stirred for about 30 minutes at about 0C-5C. The solid material was filtered and washed with water (200 mL, 4 vol). Crude wet product was obtained as yellow solid yielding 101.8 % Weight Yield (WY) (87 % Molar Yield (MY)), HPLC purity 90.8% on area at this stage. The crude material, obtained in either of the above described options, was purified through crystallization from acetone: heptane as follows: to a solution of 4-((5,6- diphenyl-pyrazin-2-yl)(isopropyl)amino)butan-1-ol crude in acetone (175 mL, 3.5 vol) at 0C – 5C, hexane (600 mL, 12 vol) dropwise in about 120 min was added, then the precipitated mixture was cooled down to about -10C and stirred for about 60 min. The product was filtered off and washed with hexane (250 mL, 5 vol) and dried under vacuum at 25C. Pure product was obtained as yellowish solid yielding overall 77.2%, (66.5% MY), HPLC purity 98.2% on area.

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; TEVA PHARMACEUTICALS INTERNATIONAL GMBH; TEVA PHARMACEUTICALS USA, INC.; VILLALVA, Nidia; CANTE, Ivon; AYBAR, Martin; RODRIGUEZ, Angel; TORRES, Alejandro, Guillen; KANTOR, Hana; GAVENDA, Ales; HERRERA, Hugo; JEGOROV, Alexander; LOPEZ, Nydia; (40 pag.)WO2017/40872; (2017); 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. 87597-21-5, name is Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H7Br2N3O2

Step B: Preparation of (6,8-dibromoimidazo[1 ,2-a]pyrazin-2-yl)methanolTo a stirred solution of ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate (13.95 g, 40mmol) in toluene (558 mL) at 0 C was added 80 mL DIBAH (120 mmol, 3 eq, 1 .5M in toluene) dropwise. After stirring overnight at rt, the solution was poured on 1M HCl, extracted with ethyl acetate and the organic phase was washed with water, sole, dried over sodium sulphate and filtered. Removal of the solvent and recrystallyzation from DCM yielded 5.55 g (45.2 %) (6,8-dibromoimidazo[1 ,2- a]pyrazin-2-yl)methanol: 1H-NMR (300 MHz, d6-DMSO): delta =8.93 (s, 1 H), 8.05 (s, 1 H), 5.46 (bs, 1 H), 4.63 (s, 2H) ppm. UPLC-MS: RT = 0.73 min; m/z 308.0 [MH+]; required MW = 307.0.

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; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80236; (2012); A1;,
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. 1209646-17-2, name is 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

5-(4-(tert-butoxycarbonyl) piperazin-1 -yl) pyrazine-2-carboxylic acid (200 mg, 0.65 mmol), tert-butyl 2-amino-4-(thiophen-2-yl) phenylcarbamate (157 mg, 0.54 mmol) and EDCI (311 mg, 1.62 mmol) were added into Py (5 ml). The mixture was stirred at room temperature for overnight. When the reaction finished, it was concentrated and washed with Et20. The yellow solid was collected as product (310 mg, 65% yield).

According to the analysis of related databases, 1209646-17-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Regenacy Pharmaceuticals, LLC; van Duzer, John H.; Mazitschek, Ralph; (123 pag.)US2018/141923; (2018); 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 58138-79-7 as follows. Recommanded Product: 58138-79-7

General procedure: OUY-2 [2], OUK-2 [3] and OUJ-2 were prepared by Stillecoupling of stannyl compound 1 [3] with 3,5-dibromopyridine,2,6-diiodopyrazine, and 2,4-dichloro-1,3,5-triazine, respectively,by using Pd(PPh3)4 as a catalyst in toluene at 110 C underan argon atmosphere (Scheme 1)

According to the analysis of related databases, 58138-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Imato, Keiichi; Enoki, Toshiaki; Uenaka, Koji; Ooyama, Yousuke; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1712 – 1721;,
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. 58138-79-7, name is 2,6-Diiodopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2,6-Diiodopyrazine

1. 2-Iodo-6-dimethylaminopyrazine A solution of 2,6-diiodopyrazine (6 g, 18.1 mmol) in methanol (50 ml) and dimethylamine (40% aqueous solution, 200 ml) was heated at reflux for 1 h. The methanol was removed under vacuum, the aqueous saturated with potassium carbonate and extracted with dichloromethane (3*100 ml). The combined extracts were dried (Na2 SO4), evaporated and the residue purified by chromatography through silica-gel eluding with dichloromethane. The product (4 g) was obtained as a low melting solid, m.p. 46-48 C., m/e 249 (M+); delta (360 MHz, CDCl3) 3.10 (6H, s, 2*Me); 7.87 (1H, s, pyrazine-H); 8.01 (1H, s, pyrazine-H).

The synthetic route of 58138-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Limited; US5260293; (1993); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 723286-80-4,Some common heterocyclic compound, 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, molecular formula is C10H15BrN4O2, 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 solution of 1 ,1-dimethylethyl 3-bromo-5,6-dihydro[1 ,2,4]triazolo[4,3-a]pyrazine- 7(8H)-carboxylate (200 mg, 0.660 mmol, commercially available) in 1 ,4-dioxane (2 ml_), 2-(tributylstannanyl)pyridine (364 mg, 0.990 mmol) was added and mixture was degassed with a stream of argon for few minutes. Pd(Ph3P)4 (38.1 mg, 0.033 mmol) was then added followed by copper(l) iodide (39.2 mg, 0.206 mmol) and the mixture was submitted to microwave irradiation heating at 130 0C for 25 minutes until the reaction was complete by LCMS. Volatiles were removed under reduced pressure and the residue was purified by chromatography on silica gel (Snap 1 1 g NH column) eluting with a gradient from 0 to 100% ethyl acetate in iso-hexane (10CV) and then with 100% ethyl acetate (7CV). A colourless oil was obtained. The product was still impure and so was further purified by chromatography on silica gel (Si 5g) eluting with a 80% ethyl acetate in iso hexane (5CV) and then with 10% MeOH in DCM (5 CV) then by chromatography on silica gel (Si column 5g) eluting first with ethyl acetate (4CV) and then with 10% MeOH in DCM (6CV). Colourless oil was obtained of the desired product in 115 mg. LCMS m/z 301.9 [M+H] (at) 0.84 min (2 min run)

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

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 58138-79-7, 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. 58138-79-7 name is 2,6-Diiodopyrazine, 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.

STAGE 2: preparation of 2-iodo-6-methoxypyrazine 2,6-Diiodopyrazine (5.0 g, 15 mmol) was added to a solution of sodium methoxide in methanol (prepared from sodium (0.35 g, 15 mmol) and methanol (40 ml)) and the mixture was heated at reflux temperature for 1 hour. After cooling, the solution was diluted with water (200 ml) and extracted with diethylether (3*100 ml). The combined extracts were washed with water, dried over magnesium sulphate and concentrated under reduced pressure to give the product as a white solid (3.5 g, 100percent) m. pt. 35.7-37.2 NMR (90 MHz, CDCl3): b 8.40 (1H, s), 8.16 (1H,s), 3.98 (3H,s). m/z 236(M+), 127, 109 (100percent).

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

Reference:
Patent; Imperial Chemical Industries, PLC; US4975112; (1990); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 87597-21-5, name is Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-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 87597-21-5, Application In Synthesis of Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate

To a stirred solution of ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate (13.95 g, 40 mmol) in toluene (558 mL) at 0 C. was added 80 mL DIBAH (120 mmol, 3 eq, 1.5M in toluene) dropwise. After stirring overnight at rt, the solution was poured on 1M HCl, extracted with ethyl acetate and the organic phase was washed with water, sole, dried over sodium sulphate and filtered. Removal of the solvent and recrystallyzation from DCM yielded 5.55 g (45.2%) (6,8-dibromoimidazo[1,2-a]pyrazin-2-yl)methanol: 1H-NMR (300 MHz, d6-DMSO): delta=8.93 (s, 1H), 8.05 (s, 1H), 5.46 (bs, 1H), 4.63 (s, 2H) ppm. UPLC-MS: RT=0.73 min; m/z 308.0 [MH+]; required MW=307.0.

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

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Koppitz, Marcus; Klar, Ulrich; Jautelat, Rolf; Kosemund, Dirk; Bohlmann, Rolf; Bader, Benjamin; Lienau, Philip; Siemeister, Gerhard; US2013/267527; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem