Tag: M.W=300-400

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 87597-21-5 as follows. SDS of cas: 87597-21-5

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.

According to the analysis of related databases, 87597-21-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80232; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature 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 0.173 g (0.571 mmol) OF 3-BROMO-7- (TERT-BUTOXYCARBONYL)- 5,6, 7,8-tetrahydro [1, 2, 4] triazolo [4, 3-a] pyrazine in 6 ML of methanol was added 0. 39 ML of 25% w/w solution of sodium methoxide in methanol. The reaction was heated at 65 C for 1 d. The reaction was diluted with ethyl acetate and washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo. The crude product was purified by flash chromatography on a BIOTAGE system (silica gel, 5% methanol/ethyl acetate) to yield the title compound. LC/MS 255.1 (M+1).

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; MERCK & CO., INC.; WO2004/58266; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 243472-70-0,Some common heterocyclic compound, 243472-70-0, name is 5-Bromo-2,3-diphenylpyrazine, molecular formula is C16H11BrN2, 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: Trimethylamine(33% ethanol solution, 358 g, 2.0 mol) was added5-chloro-2,3-diphenylpiperazine (266 g, 1.0 mol) in ethyl acetate (1.3 L)And stirred at room temperature for 48 hours.A large number of solids are present.filter,The solid was washed with ethyl acetate (2 x 50 mL)Dried in high vacuum to give 283.5 g of a white solid,The yield was 87%.:_In the same manner as in Example 1, except that 5-bromo-2,3-diphenylpiperazine was used in place of 5-chloro-2,3-diphenylpiperazine,Preparation of 2,3-diphenylpiperazine trimethylammonium bromide with 2,3-diphenylpiperazine trimethylammonium chloride.The yield was 75%.

The synthetic route of 243472-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Guohang Pharmaceutical Technology Co., Ltd.; Mei, Desheng; (11 pag.)CN106467496; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1245644-42-1, 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 1245644-42-1 as follows.

To a solution of 6-bromo-3-iodoimidazo[1,2-a]pyrazine (3.00 g, 9.26 mmol) in DMF (20 mL), was added Na2CO3 (2.46 g, 23.2 mmol), 4-chlorophenylboronic acid (1.60 g, 10.2 mmol) and Pd(PPh3)4 (214 mg, 0.18 mmol). The resulting mixture was stirred at 80 C. for 18 h under inert atmosphere and was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent Hex/EtOAc 3:2) to afford 6-bromo-3-(4-chlorophenyl)imidazo[1,2-a]pyrazine (930 mg, 32%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 9.03 (d, J=1.2 Hz, 1H), 8.36 (d, J=1.2 Hz, 1H), 7.91 (s, 1H), 7.54 (q, J=12.3 Hz, 4H); MS (ESI) m/z 308 [C13H7BrN4+H]+.

According to the analysis of related databases, 1245644-42-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Agency for Science, Technology and Research; Nacro, Kassoum; Duraiswamy, Athisayamani Jeyaraj; Rao, Lohitha; US2014/371199; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 723286-80-4, 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. 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A solution of tert-butyl 3-bromo-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylate (1 g, 3.30 mmol, 1 equiv.) in CH3NH2 (in EtOH) (7 mL) was stirred for 20 h at 100 degree Celsius. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The resulting mixture was concentrated under reduced pressure. The residue was purified by reverse phase flash with the following conditions (Column: C18 Column 120 g; Mobile Phase A: Water(10 mmol/L AcOH), Mobile Phase B: ACN; Flow rate: 50 mL/min; Gradient: 20% B to 50% B in 40 min; 254/220 nm) to afford tert-butyl 3-(methylamino)- 5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylate(550 mg, 65.82%) as a off-white solid.

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; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. Product Details of 723286-80-4

3-Bromo-5,6-dihydro-8H-[l,2,4]triazolo[4,3-a]pyrazine-7-carboxylic acid tert- butyl ester (54.8 mg, 0.181 mmol), 4-(( ^)-3-mo holin-4-yl-l-phenylsulfanyl-methyl- propylamino)-3-trifluoromethanesulfonyl-benzenesulfonamide ( 100 mg, 0.181 mmol), (IS, 25)-N,N’-dimethyl-cyclohexane-l,2-diamine (07.71 mg, 0.054 mmol), cesium carbonate (100 mg, 0.307 mmol), and copper (I) iodide (5.16 mg, 0.027 mmol) were added to a microwave vial followed by toluene (2 mL). The reaction mixture was degassed for 15 minutes under nitrogen and then heated to 90C for 14 hours. The crude material was directly purified via flash chromatography on silica gel (0-25% 7 N ammonia in methanol in CH2C12) to afford the title compound (130 mg, 92% yield). MS [m/z; (M+l)+]: 776.5

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 723286-80-4, its application will become more common.

Reference:
Patent; NOVARTIS AG; MILLER-MOSLIN, Karen; TOURE, Bakary-Barry; VISSER, Michael Scott; YUSUFF, Naeem; WO2011/29842; (2011); 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., Recommanded Product: 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

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., Product Details of 1209646-17-2

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

Electric Literature of 58138-79-7, These common heterocyclic compound, 58138-79-7, name is 2,6-Diiodopyrazine, 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.

An oven-dried sealed tube was charged with 2-bromo-4-methyl-thiazole- 5-carboxylic acid benzylamide (800 mg, 2.57 mmol, 1.0 equiv). The sealed tube was purged with nitrogen and Rieke zinc (10 mL, 10 g of zinc in 100 mL of tetrahydrofuran) was added. The reaction was heated in the microwave oven for 15 min at 100 0C. Stirring was stopped and the remaining zinc was allowed to settle. The supernatant containing the zinc reagent was transferred via syringe to a solution of 2,6-diiodopyrazine (680 mg, 2.1 mmol, 0.8 equiv), Pd(PPh3)4 (236 mg, 0.2 mmol, 7 mol%) in tetrahydrofuran (5 mL) and52 50352dimethyl formamide (0.2 mL). The reaction mixture was purged with nitrogen for 10 min, then stirred at 160 0C for 16 hr. After cooling, the solvent was removed in vacuo and the crude product was purified by column chromatography [SiO2, ethyl acetate/heptane, 10:90 to 40:60, v/v] to afford 2-(6-iodo-pyrazin-2-yl)-4-methyl-thiazoIe- 5-carboxylic acid benzylamide ( 140 mg, 13%). MS (M+H)+ = 436, R, = 1.51 min.

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

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; XENON PHARMACEUTICALS INC; WO2008/24390; (2008); A2;,
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. 1245644-42-1, name is 6-Bromo-3-iodoimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., category: Pyrazines

To a solution of 6-bromo-3-iodoimidazo[1,2-a]pyrazine (3 g, 9.26 mmol) in DMF (50 mL), were added 4-cyanophenylboronic acid 3 (1.632 g, 11.1 mmol), K3PO4 (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 petroleumether/EtOAc 1:1) to afford of 4-(6-bromoimidazo[1,2-a]pyrazin-3-yl)benzonitrile (2.5 g, 90%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) 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 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; Agency for Science, Technology and Research; Nacro, Kassoum; Duraiswamy, Athisayamani Jeyaraj; Rao, Lohitha; US2014/371199; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem