Category: 63744-22-9

Related Products of 63744-22-9, 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. 63744-22-9 name is 6,8-Dibromoimidazo[1,2-a]pyrazine, 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 mixture of 3,4-dimethoxyaniline (18.0 g, 118 mmol), 6,8- dibromoimidazo[1 ,2-a]pyrazine (25.0 g, 90.4 mmol), and Lambda/,Lambda/-diisopropylethylamine (11.7 g, 90.4 mmol) in DMF (500 ml_) was stirred at 120 0C overnight. After this time, the reaction was cooled to room temperature and concentrated to approximately 100 ml_ under reduced pressure. The dark brown reaction mixture was poured into ice-cold water (300 ml_) and stirred for 10 min. The resulting brown precipitate was filtered and the filter cake washed with water (100 ml_). The filter cake was dried under vacuum and recrystallization from methanol (-800 ml_) to afford 6-bromo-Lambda/-(3,4,5- trimethoxyphenyl)imidazo[1 ,2-a]pyrazin-8-amine (2) (23.3 g, 74%) as a light brown needle-shaped solid: 1H NMR (300 MHz, DMSO-Gf6) 9.81 (s, 1 H), 8.22 (s, 1 H), 7.93 (s, 1 H), 7.75 (d, J = 2.4 Hz, 1 H), 7.62 (s, 1 H), 7.53 (dd, J= 8.7, 2.4, 1 H), 6.94 (d, J= 8.7 Hz, 1 H), 3.77 (s, 3H), 3.75 (s, 3H); ESI MS m/z 349.2 [M + H]+; HPLC, 6.92 min, >99% (AUC).

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; CGI PHARMACEUTICALS, INC.; MITCHELL, Scott A.; CURRIE, Kevin S.; BLOMGREN, Peter A.; KROPF, Jeffrey E.; LEE, Seung H.; XU, Jianjun; STAFFORD, Douglas G.; HARDING, James P.; BARBOSA, Jr., Antonio J.; ZHAO, Zhongdong; WO2010/68257; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63744-22-9, 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 63744-22-9 as follows.

Diisopropylethylamine (2.4 mL, 13.62 mmol) and cyclopropylamine (943 muL, 13.62 mmol) were added to commercially available (Ark Pharm, Inc.) 6,8-dibromoimidazo[1,2-a]pyrazine (2.51 g, 9.08 mmol) dissolved in 2-propanol (9 mL). The solution was placed in an 80 C. oil bath. After 4.5 h, the volatiles were removed in vacuo. The brown residue was partitioned between dichloromethane (50 mL) and water (50 mL). The organic layer was washed further with water (50 mL) and then brine (50 mL). The organic layer was dried over MgSO 4, filtered and concentrated in vacuo. The residue was purified via a filtration over a short plug of silica gel (40% EtOAc/hexanes) and the filtrate was concentrated in vacuo to afford 6-bromo-N-cyclopropylimidazo[1,2-a]pyrazin-8-amine (2.19 g, 95%) as a light brown solid.

According to the analysis of related databases, 63744-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SENHWA BIOSCIENCES INCORPORATED; HADDACH, MUSTAPHA; TRAN, JOE A; PIERRE, FABRICE; REGAN, COLLIN F; RAFFAELE, NICHOLAS B; RAVULA, SUCHITRA; RYCKMAN, DAVID M; (482 pag.)JP5802676; (2015); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63744-22-9, 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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

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- ajpyrazine (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 (1 H, s), 8.00 (1 H, d), 7.66 (1 H, d2.54 (3H, s) ppm.

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-Dibromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80234; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 63744-22-9,Some common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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 4-(4-(oxetan-3-yl)piperazin-1-yl)-3-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)aniline XXIV (619 mg, 2.17 mmol) and 6,8-dibromoimidazo[1,2-a]pyrazine (601 mg, 2.2 mmol) in IPA (15 mL) was added N,N-Diisopropylethylamine (0.95 ml, 5.43 mmol). The mixture was stirred at 110 C. for 16 h. After this time, DCM (10 mL) and sat aqueous NaHCO3 (15 mL) were added. The aqueous layer was separated and extracted with DCM (2*10 mL). The combined organic extracts were washed with brine (10 mL) and dried over sodium sulfate. The resulting residue was purified by column chromatography ISCO Rf (24 g column) eluting with a gradient of 100% DCM-60:35:5 DCM:Et2O:MeOH to provide 6-bromo-N-(4-(4-(oxetan-3-yl)piperazin-1-yl)-3-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl)imidazo[1,2-a]pyrazin-8-amine XXV.

The synthetic route of 63744-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Lo, Jennifer R.; Mitchell, Scott A.; Schmitt, Aaron C.; Xiong, Jin-Ming; Xu, Jianjun; Zhao, Zhongdong; US2015/175616; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63744-22-9, The chemical industry reduces the impact on the environment during synthesis 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

Intermediate Example15-1 Preparation of 6,8-dibromo-3-iodo-imidazo[ 1 ,2-a]pyrazinTo a stirred solution of intermediate example 1-1 (8.7 g g, 31.4 mmol) in DMF (210 mL) was added NIS (7.42 g, 33 mmol, 1.05 eq) in one portion at rt. After 18 h stirring at 60C, the solvent was removed in vaccuo and the residue was taken up in DCM and washed with water and saturated sodium thiosulfate solution. The organic phase was dried over sodium sulphate, filtered and the solvent was evaporated to yield 9.46 g (74.8 ¾) 6,8-Dibromo-3-iodo-imidazo[1 ,2-a]pyrazine: 1H-NMR (300 MHz, CDCb): delta = 8.22 (1 H, s), 7.91 (1 H, s) ppm.

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-Dibromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

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

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 63744-22-9 as follows. Recommanded Product: 63744-22-9

Intermediate Example 16-Bromo-8-(methylsulfanyl)imidazo 1 ,2-a]pyrazineA mixture of 61 .0 g (220 mmol) 6,8-dibromoimidazo[1 ,2-a]pyrazine (CAS 63744- 22-9), 610 mL methanol and 30.2 g sodium methanethiolate was stirred at 23 C for 16 hours, poured into 6 L water and cooled until a precipitate had formed. The product was filtered off and dried at 60C to give 38.5 g (72%) of the title compound which was used without further purification.

According to the analysis of related databases, 63744-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KLAR, Ulrich; KOPPITZ, Marcus; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; PRECHTL, Stefan; NGUYEN, Duy; SCOTT, William; WO2011/113862; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63744-22-9, 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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

[0293] (R)-(4-(4-((6-Bromoimidazo[1,2-a]pyrazin-8- yl)amino)phenyl)morpholin-2-yl)methanol XVII: In a 250 mL round bottom flask equipped with a condenser was placed 6,8-dibromoimidazo[1,2-a]pyrazine (2000 mg, 7.22 mmol) and added 30 mL isopropanol followed by N,N-diisopropylethylamine (2.52 ml, 14.44 mmol) and (R)-(4-(4-aminophenyl)morpholin-2-yl)methanol (1504.12 mg, 7.22 mmol). The reaction was heated to reflux (oil bath 95 C) overnight. The reaction was cooled and precipitates were collected by filtration and washed with isopropanol followed by hexanes to give the desired compound XVII, 2.92 g, 95% yield.

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.; 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

Application of 63744-22-9,Some common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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.

(R)-(4-(4-((6-Bromoimidazo[1,2-a]pyrazin-8-yl)amino)phenyl)morpholin-2-yl)methanol XVII In a 250 mL round bottom flask equipped with a condenser was placed 6,8-dibromoimidazo[1,2-a]pyrazine (2000 mg, 7.22 mmol) and added 30 mL isopropanol followed by N,N-diisopropylethylamine (2.52 ml, 14.44 mmol) and (R)-(4-(4-aminophenyl)morpholin-2-yl)methanol (1504.12 mg, 7.22 mmol). The reaction was heated to reflux (oil bath 95 C.) overnight. The reaction was cooled and precipitates were collected by filtration and washed with isopropanol followed by hexanes to give the desired compound XVII.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6,8-Dibromoimidazo[1,2-a]pyrazine, its application will become more common.

Reference:
Patent; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Lo, Jennifer R.; Mitchell, Scott A.; Schmitt, Aaron C.; Xiong, Jin-Ming; Xu, Jianjun; Zhao, Zhongdong; US2015/175616; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 63744-22-9, 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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

11d (0.5 g, 2.8 mmol), 1a (0.8 g, 2.8 mmol), isopropanol (5.1 ml), and diisopropylethylamine (0.7 g, 5.6 mmol) were added to a 25 ml three-necked flask. The system was replaced with nitrogen for three times under stirring. The system was refluxed for 16 hours in 100 C oil bath. The system was cooled to 17 C, and concentrated to dryness under reduced pressure, purified by silica gel column chromatography (ethyl acetate / n-hexane = 1/10 to 1: 3) to give light yellow solid Compound 11e (0.7 g, 99.5% purity, yield 72.6%). MS m/z 374.0 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 6,8-Dibromoimidazo[1,2-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hangzhou Innogate Pharma Co., Ltd.; ZHANG, Hancheng; LIU, Shifeng; YE, Xiangyang; CHEN, Wenting; (53 pag.)EP3553065; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 63744-22-9, 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. 63744-22-9 name is 6,8-Dibromoimidazo[1,2-a]pyrazine, 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.

EXAMPLE 1Part A: The title compound was prepared according to US20060106023 (A1 ).

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; SCHERING CORPORATION; ALBANY MOLECULAR RESEARCH, INC.; WO2009/97233; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem