Category: 63744-22-9

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, Product Details of 63744-22-9

To a solution of 4-(4- (oxetan-3-yl)piperazin- l-yl)-3-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)aniline XXIV (619 mg, 2.17 mmol) and 6,8-dibromoimidazo[l,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 NaHC03 (15 mL) were added. The aqueous layer was separated and extracted with DCM (2 x 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 : Et20 : MeOH to provide 6-bromo-N- (4-(4-(oxetan-3-yl)piperazin-l-yl)-3-(2-((tetrahydro-2H-pyran-2- yl) oxy)ethoxy)phenyl)imidazo [ 1 ,2- a] pyrazin- 8 -amine XXV .

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; GILEAD SCIENCES, INC.; 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, Jiangjun; ZHAO, Zhongdong; WO2015/100217; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

Step 1. Preparation of [4-(6-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-phenyl]-morpholin-4-yl-methanone A solution of 6,8-dibromoimidazo[1,2-a]pyrazine (500 mg, 1.8 mmol), (4-aminophenyl)(morpholino)-methanone (408 mg, 1.98 mmol) and CSA (356 mg, 1.53 mmol) in iPrOH (30 mL) was stirred at 90 C. overnight. The solvent was evaporated. The residue was dissolved in DCM (30 mL). A NaHCO3 solution (10 mL) was added to adjust to pH=8. The organic layer was separated and dried over Na2SO4. The drying agent was removed by filtration and the resultant solution was concentrated in vacuo. The residue was purified through a silica-gel column (ethyl acetate:petroleum ether=1:1) to give the desired product as a yellow solid (500 mg, 69% yield). LC-MS: 404 [M+1]+, tR=1.409 min.

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

Reference:
Patent; Hoffmann-La Roche Inc.; Brotherton-Pleiss, Christine E.; Lopez-Tapia, Francisco Javier; Lou, Yan; US2013/150360; (2013); A1;,
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, 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: 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

These common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[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. Safety of 6,8-Dibromoimidazo[1,2-a]pyrazine

To a solution of 6,8-dibromoimidazo[l,2-a]pyrazine (0.50 g, 1.8 mmol) [Combi- Blocks, OR-7964] in DMF (12 mL) was added N-iodosuccinimide (0.45 g, 2.0 mmol). The reaction mixture was then heated at 60 C for 15.5 h. The reaction mixture was concentrated in vacuo. The resulting solid was taken up into dichloromethane (DCM). The organic layer was washed sequentially with water and sat. Na2S203 (aq). The organic layer was then dried over Na2S04, filtered, and concentrated to afford the title compound as a light yellow solid (0.64 g, 88%). LCMS for CeltBrzINs (M+H)+: calculated m/z = 401.8, 403.8, 405.8; found 401.8, 403.7, 405.6.

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; INCYTE CORPORATION; DOUTY, Brent; BUESKING, Andrew W.; BURNS, David M.; COMBS, Andrew P.; FALAHATPISHEH, Nikoo; JALLURI, Ravi Kumar; LEVY, Daniel; POLAM, Padmaja; SHAO, Lixin; SHEPARD, Stacey; SHVARTSBART, Artem; SPARKS, Richard B.; YUE, Eddy W.; (355 pag.)WO2019/79469; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

Example 10-1 :Preparation of 6,8-dibromo-3-iodo-imidazo[1 ,2-a]pyrazine To 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 60 C, 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 %) 6,8-dibromo-3-iodo-imidazo[1,2-a]pyrazine: 1H-NMR (300 MHz, CDCb): delta = 8.22 (1H, s), 7.91 (1H, s) ppm.

The synthetic route of 63744-22-9 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

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.

Into a 250-mL 3 -necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, were placed 6,8-dibromoimidazo[l,2-a]pyrazine (5 g, 18.06 mmol, 1.00 equiv) and /V, /V-di methyl formam i dc (125 mL). This was followed by the addition of (0249) NIS (4.3 g, 19.11 mmol, 1.05 equiv), in portions at room temperature. The resulting solution was stirred overnight at 60 C in an oil bath. The reaction mixture was cooled to room temperature with a water/ice bath and then quenched with water. The resulting solution was extracted with ethyl acetate and the organic layers combined and concentrated under vacuum. Purification by flash chromatography (silica gel column with ethyl (0250) acetate/petroleum ether (1/2)) provided 2.8 g (38%) of 5-1 as a white solid.

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; IDEAYA BIOSCIENCES, INC.; BECK, Hilary, Plake; GONZALEZ-LOPEZ, Marcos; SUTTON, James, Clifford, Jr.; (86 pag.)WO2019/156989; (2019); 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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 6,8-Dibromoimidazo[1,2-a]pyrazine

Example 23A 6-({2-[(6-Bromoimidazo[1,2-a]pyrazin-8-yl)amino]ethyl}amino)pyridine-3-carbonitrile 8 g (28.9 mmol) of 6,8-dibromoimidazo[1,2-a]pyrazine were dissolved in 80 ml of DMSO, and 16.1 ml (115.6 mmol) of triethylamine and 5.154 g (31.78 mmol) of 6-[(2-aminoethyl)amino]pyridine-3-carbonitrile (Example 2A) were added. The mixture was heated at 140 C. in a microwave for 1.5 h. The solution was poured into water and the precipitate was filtered off. Washing with water and drying under high vacuum gave 10.3 g (94% of theory) of the product as a solid. LCMS (method 8): Rt=0.97 min. (m/z=358 (M+H)+). 1H-NMR (400 MHz, DMSO-d6): delta=8.39 (s, 1H), 8.08 (s, br, 1H), 8.03 (s, 1H), 7.83 (s, 1H), 7.73 (m, 2H), 7.51 (s, 1H), 6.56 (s, br, 1H), 3.5-3.65 (m, 4H).

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 63744-22-9.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/53929; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

Intermediate Example 10-1 : Preparation of 6,8-dibromo-3-iodo-imidazo[1 ,2- aj yrazineTo 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 60 C, 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 %) 6,8-Dibromo-3-iodo-imidazo[1 ,2-a]pyrazine: 1H- NMR (300 MHz, CDC ): delta = 8.22 (1 H, s), 7.91 (1 H, s) ppm

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; WO2012/80234; (2012); A1;,
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, HPLC of Formula: C6H3Br2N3

Step-(iii): Synthesis of (4-((6-bromoimidazo [1, 2-a] pyrazin-8-yl) amino) phenyl)(morpholino) methanone:To a stirred solution of Intermediate-lOb (7.0 g, 19.6 mmol), Intermediate-8b (4.0 g, 19.6 mmol) in 70 mL of DMF was added, DIPEA (10.68 mL, 58.82 mmol) and stirred at 110C for 20h. The reaction mixture was distilled under a reduced pressure to remove the solvent. Theresidue was taken in water and extracted with DCM (2 x 250 mL). The combined organic phases were washed with brine, dried over sodium sulphate and concentrated. The obtained crude product was purified by colunm chromatography using 100-200 mesh silica gel and 5% MeOH in DCM as eluent to give the titled product as a pale brown viscous solid (4.8 g, 61%); 1H NMR (400 MHz, DMSO-d6): oe 10.21 (s, 1H), 8.33 (s, 1H), 8.07 (d, 2H, J=8 Hz), 7.98 (s, 1H), 7.97 (s,1H), 7.43 (d, 2H, J=8.8 Hz), 3.61-3.5 1 (m, 8H); MS (ES) m/z 402 (M+1).

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; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BORUAH, Anima; HOSAHALLI, Subramanya; PANIGRAHI, Sunil Kumar; WO2014/125410; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem