Month: September 2021

Related Products of 768-05-8, A common heterocyclic compound, 768-05-8, name is Pyrazinoic acid hydrazide, molecular formula is C5H6N4O, 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.

In a dried RB flask, KOH (1.42 g, 25.33 mmol) was suspended in ethanol (50 mL) atambient temperature. Then pyrazine-2-carbohydrazide6a (5 g, 36.19 mmol) was added and reaction mass was cooled.Carbon disulfide (2.4 mL, 39.81 mmol)was added dropwise and the resulting mixture was refluxed for 12 h. Thereaction progress was monitored by TLC and after completion of the reactionsolvent was distilled under vacuum. The reaction pH was adjusted to 6.0-7.0 by adding4N HCl. The precipitated solid was collected by filtration, washed with water(50 mL) and dried to give white solid compound 7a. Yield: 5.71 g, 87 %; 1HNMR (CDCl3, 400 MHz, delta inppm): 14.817 (s, 1H, -SH), 9.193 (bs, 1H, Ar-H), 8.793 (s, 1H, Ar-H), 8.764 (s,1H, Ar-H); 13C NMR (100 MHz, CDCl3) delta (ppm): 168.7, 164.2, 152.6, 147.7, 145.4, 143.5; ESI-MS (m/z)= 181.1 (M+H)+; calculated for C6H4N4OS;C, 39.99; H, 2.24; N, 31.09; S, 17.80. Found: C, 39.97; H, 2.25; N, 31.05; S,17.84.

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; Reddyrajula, Rajkumar; Dalimba, Udayakumar; Bioorganic and Medicinal Chemistry Letters; vol. 30; 2; (2020);,
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. 6863-74-7, name is 6-Chloropyrazine-2-carbonitrile belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. 6863-74-7

A mixture of tert-butyl ((1R,4R,7R)-2-(1-(azetidin-3-ylmethyl)-2-(1- (cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1H-benzo[d]imidazole- 5-carbonyl)-2-azabicyclo[2.2.1]heptan-7-yl)carbamate (15 mg, 0.024 mmol), 6- chloropyrazine-2-carbonitrile (3.34 mg, 0.024 mmol), cesium carbonate (15.62 mg, 0.048 mmol), BINAP (0.746 mg, 1.199 mmol) and Pd2(dba)3 (1.098 mg, 1.199 mmol) in degassed dioxane (1.0 mL) under nitrogen in a seal vial was stirred at 90C for 18 hour. The mixture was diluted with EtOAc (5 mL) and was washed with a solution of aqueous saturated sodium bicarbonate (5 mL). The organic layer was dried over sodium sulfate and concentrated to give crude tert-butyl ((1R,4R,7R)-2-(1-(azetidin-3-ylmethyl)-2-(1- (cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1H-benzo[d]imidazole- 5-carbonyl)-2-azabicyclo[2.2.1]heptan-7-yl)carbamate (15 mg, 0.024 mmol). Material was used as is in next reaction.

The synthetic route of 6863-74-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NGU, Khehyong; (435 pag.)WO2020/33514; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 74290-67-8, 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. 74290-67-8 name is 2-Amino-5-bromo-3-methylpyrazine, 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.

a) 3-(N-(3-((5-amino-6-methylpyrazin-2-yl)ethynyl)-2,4-difluorophenyl)sulfamoyl)-5-chloro-2-methoxybenzyl Acetate A mixture of 5-chloro-3-(N-(3-ethynyl-2,4-difluorophenyl)sulfamoyl)-2-methoxybenzyl acetate (200 mg), dichlorobis(tricyclohexylphosphine)palladium(II) (34.3 mg), DIPEA (2 mL), copper(I) iodide (17.7 mg), 5-bromo-3-methylpyrazin-2-amine (114 mg) and DMSO (2 mL) was stirred under microwave irradiation at 100 C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (216 mg). MS: [M+H]+ 537.0.

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

14508-49-7, name is 2-Chloropyrazine, 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: 14508-49-7

A mixture of CHLOROPYRAZINE (9.6 g, 83.3 MMOL) and hydrogen peroxide solution (30%, 16 mi) in glacial acetic acid (26 ml) was heated at 70 C for 18 hours. The mixture was allowed to cool to room temperature, poured into water (250 ml) and extracted with DICHLOROMETHANE (3 x 100 ML). The DICHLOROMETHANE extracts were combined, washed with saturated sodium bicarbonate solution (2 x 70 ML), water (3 x 100 ML) and brine (100 ml). The organic portion was dried under sodium sulfate and evaporated in vacuo to give a white solid which was recrystallised from absolute ethanol to give the title compound (0.45 g). ‘H NMR (CDCI3) 8.27-8. 26 (1H, d), 8.15 (1 H, S), 8.03-8. 02 (1 H, dd).

The synthetic route of 14508-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/56369; (2004); 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. 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

Step 1: Synthesis of Intermediate 1-4.1R8 (212 g, 1151 mmol) in tetrahydrofuran (dry) (600 mL) is cooled to -78°C. Then n-butyllithium(2.5 M in hexanes, 552 mL, 1381 mmol) is added dropwise, keeping the temperature below -78°C.After 30 mm R9 (324g, 1209 mmol) in tertahydrofuran (dry) (120 mL) is added dropwise. Thereaction mixture is stirred at -78°C for 1 h. The mixture is quenched with saturated NH4C1 solutionand extracted three times with ethyl acetate. The organic layer is washed with brine, dried overNa2SO4 and evaporated in vacuo. The residue is purified by flash chromatography (heptane/ ethyl acetate = 80/20). Yield 60percent.

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 109838-85-9.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140091; (2014); 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. 56423-63-3, name is 2-Bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

General procedure: Method S Parallel preparation of Examples 39-40: To a set of vials containing the requisite aryl bromide (0.12 mmol) was added bis[(tetrabutylammonium iodide)copper(I) iodide] (3.9 mg, 0.0034 mmol), 1,10 phenanthroline (2.5 mg, 0.014 mmol) followed by Cs2C03 (68 mg, 0.21 mmol). The vials were capped and transferred into a glove box under an atmosphere of nitrogen. To each vial was added a solution of H2 (30 mg, 0.069 mmol) in dioxane (1.0 mL). The vials were capped and the mixtures were heated at 100 C with stirring overnight. After that time, the mixtures were allowed to cool to RT. To each vial was added water (2 mL) and DCM (2 mL). The mixtures were transferred to a set of fritted barrel filters. The organic layer from each mixture was drained into a clean vial. Additional DCM (1 mL) was added to each aqueous layer and the organic layer was again drained and combined with the previous organic extract. The solvent from the combined organic layers was removed in vacuo. The crude residues were dissolved in DMSO (1 mL) and filtered. The crude products were purified by mass triggered reverse phase HPLC using the following conditions: [column: Waters XBridge CI 8, 5muiotaeta, 19×100 mm; solvent gradient: 19-21% initial to 49-51% final MeCN (0.1% NH4OH) in water (0.1% NH4OH) 25 mL/min; 8 min run time] to afford Examples 39-40.

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 56423-63-3.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; CUMMING, Jared, N.; LIU, Hong; SCOTT, Jack, D.; (0 pag.)WO2016/85780; (2016); 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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Chloropyrazine-2-carboxylic acid

N,N-dimethylformamide (1 drop) is added to a flask charged with a stir bar, 5-chloro- pyrazine-2-carboxylic acid (13.17 g), thionyl chloride (25 mL), and toluene (200 mL) at room temperature. The mixture is stirred at 60 00 overnight. After cooling to room temperature, the mixture is concentrated, and the remainder is freed from volatile residues by three times repeated evaporation with toluene.

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 36070-80-1.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; WAGNER, Holger; (77 pag.)WO2018/138028; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 24241-18-7, 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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Intermediate Example 1 -1 :Preparation of 6,8-dibromo-imidazo[1 ,2-a]pyrazineTo a stirred suspension of 2-amino-3,5-dibrompyrazine (427 g, 1688mmol) in water (6.4 L) / THF (482 ml_), at rt was added bromacetaldehyde-diethylacetal (998 g, 5065 mmol) in one portion. After stirring under reflux for 4 h, the clear orange solution was stirred for an additional 15 h at rt. The suspension was filtered, and the remaining solid was washed with MeOH (2 L) and dried in vaccuo at 60 C to yield 6,8-dibromo-imidazo[1 ,2-a]pyrazine as an off-white solid (500 g, 107% with residual MeOH): 1H-NMR (300 MHz, d6-DMSO): delta =9.02 (s, 1 H), 8.23 (d, 1 H), 7.89 (d, 1 H) ppm. UPLC-MS: RT = 0.80 min; m/z 277.9 [MH+]; required MW = 276.9.

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

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

Some common heterocyclic compound, 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, molecular formula is C6H3BrClN3, 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. SDS of cas: 143591-61-1

[00274] 3-(Trifluoromethyl)phenol (1.57 mL, 12.95 mmol) was added to a suspension of sodium hydride (706 mg, 17.65 mmol – 60% in mineral oil) in anhydrous DMF (30 mL) and the resulting mixture was stirred for 40 minutes. A solution of 3-bromo-8-chloroimidazo[l,2- ajpyrazine (2.731 g, 11.75 mmol) in anhydrous DMF (30 mL) was added to the reaction mixture and stirred overnight at room temperature. The reaction mixture was diluted with water and the resulting precipitate was filtered off and washed with water and then hexane to give 3-bromo-8-(3-(trifluoromethyl)phenoxy)imidazo[l,2-a]pyrazine (3.4g, 81%) as a white solid. LCMS MH+ 359.8. 1H NMR (d6-DMSO): 8.20 (IH, d, J 4.7), 7.96 (IH, s), 7.64-7.77 (4H, m), 7.52 (IH, d, J4.7).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 143591-61-1, its application will become more common.

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; PRICE, Paul Damien; MIDDLETON, Penny; WO2010/69684; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 77168-85-5, 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. 77168-85-5, name is Methyl 5-chloro-6-methylpyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: methyl 5-(5-fluoro-2-methoxypyridin-4-yl)-6-methylpyrazine-2-carboxylate To a nitrogen-purged solution of methyl 5-chloro-6-methylpyrazine-2-carboxylate (15 g, 80 mmol), (5-fluoro-2-methoxypyridin-4-yl)boronic acid (16.49 g, 96 mmol), Pd (dppf) Cl2 dichloromethane adduct (1.2 g,1.469 mmol) and Pd(dppf)C12 (4.6 g, 6.29 mmol) in THF (199 ml) and water (40.8 ml) was addedpotassium phosphate tribasic (51.2 g, 241 mmol) under a nitrogen atmosphere. A reflux condenserwas attached and the mixture was vigorously refluxed with a 100 °C oil bath with stirring. After 105mm, the reaction was cooled to rt and partitioned between EtOAc (200 mL) and water (200 mL).The layers were separated and the aqueous layer was extracted with ethyl acetate (150 mL). Theorganic layers were combined, filtered through C eliteTM, washed with brine, dried over anhydrousMg504, filtered and evaporated to afford a crude residue. The resulting residue was purified via column chromatography on silica gel (ISCO RediSep Gold 330g silica gel column, gradient elution with 0percent to 50percent EtOAc in hexanes) to give the title compound.

The chemical industry reduces the impact on the environment during synthesis Methyl 5-chloro-6-methylpyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHEN, Helen; COLLETTI, Steven, L.; DEMONG, Duane; GUO, Yan; MILLER, Michael; NAIR, Anilkumar; PLUMMER, Christopher, W.; XIAO, Dong; YANG, De-Yi; (289 pag.)WO2016/22742; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem