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Sources of common compounds: 3-Bromo-8-chloroimidazo[1,2-a]pyrazine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, its application will become more common.

Related Products of 143591-61-1,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.

Example 13 – N-fS-fS-fCvclohexylamino^midazop^-alpyrazin-S-ypphenvpacetamide (Compound 165)[00260] 3-Bromo-8-bromo/chloroimidazo[l,2-a]pyrazine (200 mg, 0.86 mmol) was combined with JV,iV-diisopropylethylamine (750 uL, 4.3 mmol), cyclohexylamine (1.97 mL, 17.2 mmol) and THF (4 mL) and the mixture heated in a sealed tube at 7O C for 16 hours. In a separate reaction, 3-bromo-8-chloroimidazo[l,2-a]pyrazine (200 mg, 0.86 mmol) was combined with N,N-diisopropylethylamine (750 uL, 4.3 mmol), cyclohexylamine (0.49 mL, 4.3 mmol) and THF (4 mL) and the mixture heated in a sealed tube at 7O C for 16 hours. The reactions were worked up separately. Upon cooling, the reaction mixtures were partitioned between DCM and water and the orgranic extract washed with water and brine, dried over MgSO4, and concentrated in vacuo. The crude products were then combined and purified by column chromatography (EtO Ac/petroleum ether) to give 3-bromo-N-cyclohexylimidazo [l,2-a]pyrazin-8-amine (372 mg, 73%). LCMS RT= 1.66min, MH+ 296.9. 1U NMR (d6- DMSO): 7.45-7.47 (2H, m), 7.38 (IH, d, J4.8), 5.85-7.87 (IH, m), 4.10 (IH, m), 2.10-2.16 (2H, m), 1.77-1.84 (2H, m), 1.62-1.72 (IH, m), 1.26-1.52 (5H, m).

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

Brief introduction of 3-Bromo-8-chloroimidazo[1,2-a]pyrazine

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, 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Related Products of 143591-61-1, The chemical industry reduces the impact on the environment during synthesis 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

Method B 3-Bromo-?/-(3′-(trifluoromethyl)phenyl)imidazori,2-alpyrazin-8-amine [00247] Sodium hydride (84 mg, 2.10 mmol – 60% in mineral oil) was dissolved in DMSO (2mL). 3-(Trifluoromethyl)aniline (340 mg, 0.263 mL, 2.11 mmol) was then added and the resulting mixture was stirred at room temperature under a nitrogen gas atmosphere for 10 minutes. A solution of 3-bromo-8-bromo/chloroimidazo[l,2-a]pyrazine (245 mg, 1.05 mmol) in DMSO (2 mL) was then added and stirring at room temperature under a nitrogen gas atmosphere continued for another 2 hours. The reaction was quenched by the addition of saturated ammonium chloride solution (aq.) followed by extraction into EtOAc. The organic extracts were washed with brine, dried and concentrated in vacuo. Purification by flash column chromatography (gradient 7:1 to 6:1 40-60 petrol :EtO Ac) followed by trituration with 40-60 petrol gave the title compound (98 mg, 26%) as a white powder. 1H NMR (d6- DMSO): 10.12 (IH, s), 8.58 (IH, br s), 8.32 (IH, d, J 8.5 Hz), 7.88 (IH, d, J4.6), 7.85 (IH, s), 7.63 (IH, d, J4.7), 7.56 (IH, t, J7.9), 7.35 (IH, d, J7.8).

Application of 143591-61-1

The synthetic route of 143591-61-1 has been constantly updated, and we look forward to future research findings.

Electric Literature of 143591-61-1, These common heterocyclic compound, 143591-61-1, name is 3-Bromo-8-chloroimidazo[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.

3-bromo-8-chloroimidazo [1,2-a] pyrazine (1.33 g, 5.7 mmol),1- (2-methoxyethyl) -1H-pyrazole-4-amine (0.96 g, 6.8 mmol) was added to 15 mL of n-butanol,The temperature was raised to 120 C and reacted overnight.The solvent was removed by rotary evaporation, diluted with 30 mL of water, and extracted with ethyl acetate (20 mL * 3). The organic phases were combined,It was washed with 20 mL of saturated brine, dried over anhydrous sodium sulfate, and concentrated.Separation through a silica gel column gave 1.45 g of a pale yellow solid with a yield of 76%.

The synthetic route of 143591-61-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Xing Qingfeng; Ai Yixin; (85 pag.)CN110272426; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Introduction of a new synthetic route about 143591-61-1

The synthetic route of 143591-61-1 has been constantly updated, and we look forward to future research findings.

Example 103; To a solution of compound 102 (13.0 g, 55.9 mmol) in DMSO (150 mL) was added sodium methanethiolate (4.70 g, 67.08 mmol) as a DMSO solution (100 mL) at room temperature. The reaction mixture was stirred at 100 C. for 16 hours. The mixture was cooled to 25 C. and added to a brine solution (300 mL), and extracted with 10% IPA/dichloromethane (300 mL, 3¡Á). The combined organic layer was dried over anhydrous sodium sulfate and concentrated. Purification by column chromatography (SiO2, ethyl acetate/hexanes (1:1)) afforded compound 103 as a yellow solid 10 g (70%). 1H-NMR (400 MHz, DMSO-d6 delta 8.15 (d, 1H), 7.88 (d, 1H), 7.83 (s, 1H), 2.6 (s, 3H).

The synthetic route of 143591-61-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US2007/117804; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Continuously updated synthesis method about 143591-61-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 143591-61-1, name is 3-Bromo-8-chloroimidazo[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 143591-61-1, Formula: C6H3BrClN3

A 33% (w/v) ethanol solution of methylamine (5.4 mL,130.55 mmol)was added to a solution of 3-bromo-8-chloroimidazo[1,2-a]pyrazine (500 mg, 2.15 mmol) in ethanol in a microwaveadaptedvial. The reaction was submitted to microwave irradiationsduring 20 min at 140 C. The solvent was removed underreduced pressure. The crude mixture was dissolved in ethyl acetateand successively washed with saturated aqueous chloride ammonium,distilled water and finally brine. The organic phase was driedon sodium sulphate, filtered and concentrated under reducedpressure. The compound is obtained as a white solid (92% yield). C7H7BrN4. Mw: 227.06 g/mol. Mp 145-146 C. 1H-RMN delta (ppm,400 MHz, DMSO-d6) 2.94 (d, 3H, NHCH3, J 6 Hz), 7.42 (d, 1H, CH 6,J 8 Hz), 7.52 (d, 1H, CH 7, J 8 Hz), 7.65 (m, 2H, NH, CH 2). 13CRMNdelta (ppm, 100 MHz, DMSO-d6) 22.77 (NHCH3), 97.83 (Cq 1),107.34 (CH 7),130.04 (CH 6),132.10 (CH 2),133.81 (Cq 3′),150.72 (Cq4). MS (ESI+ , QTof, m/z): 227.1 [M+H]+. HRMS calculated forC7H8BrN4 226.9932, found 226.9935.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Article; Patinote, Cindy; Bou Karroum, Nour; Moarbess, Georges; Deleuze-Masquefa, Carine; Hadj-Kaddour, Kamel; Cuq, Pierre; Diab-Assaf, Mona; Kassab, Issam; Bonnet, Pierre-Antoine; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 909 – 919;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A new synthetic route of 143591-61-1

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-8-chloroimidazo[1,2-a]pyrazine. I believe this compound will play a more active role in future production and life.

Electric Literature of 143591-61-1, 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. 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

In a 2000ml three-necked flask, with mechanical stirring, Ar gas protection. Join4.62 g of 3-bromo-8-chloroimidazo [1,2-a] pyrazine (molecular weight 231, 0.02 mol)5.6 g (molecular weight 254.2, 0.022 mol) of bis (pinacolato) diboron, 23.2 g (0.0044 mol) of Pd (dppf) Cl, 36 g (molecular weight 138,1,4-dioxane 500ml. Start mechanical stirring,After 3 times of evacuation under reduced pressure to maintain Ar gas protection,The reaction was monitored by TLC (thin layer chromatography)Until the complete disappearance of raw materials, reflux for 3 hours, the reaction was complete. Let cool, the reaction system divided into two layers, the organic layer was separated and evaporated to dryness to give 5.04g product, yield 90.2%.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Li Yinkui; Tang Jinming; Fan Hongtao; (34 pag.)CN104650116; (2017); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Extracurricular laboratory: Synthetic route of 143591-61-1

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.

Ammonia of a 30% (w/v) aqueous solution (2.3 mL, 57.37 mmol)was added to a solution of 3-bromo-8-chloroimidazo [1,2-a]pyrazine(500 mg, 2.15 mmol) in acetonitrile in a microwave-adaptedvial. The reaction was submitted to microwave irradiations during2 h at 140 C. The solvent is removed under reduced pressure. Thecrude mixture was dissolved in ethyl acetate and successivelywashed with saturated aqueous chloride ammonium, distilledwater and finally brine. The organic phase was dried on sodiumsulphate, filtered and concentrated under reduced pressure. Thecompound is obtained as a white solid (87% yield). C6H5BrN4. Mw:213.03 g/mol. Mp 242-243 C. 1H-RMN delta (ppm, 400 MHz, DMSOd6)7.10 (s, 2H, NH), 7.36 (d, 1H, CH 6, J = 8 Hz), 7.56 (d, 1H, CH 7,J = 8 Hz), 7.65 (s, 1H, CH 2). 13C-RMN delta (ppm, 100 MHz, DMSO-d6)97.81 (Cq 1), 108.03 (CH 7), 130.19 (CH 6), 132.45 (CH 2), 133.46 (Cq30), 150.72 (Cq 4). MS (ESI+ , QTof, m/z): 213.1 [M+H]+. HRMScalculated for C6H6BrN4 212.9776, found 212.9785.

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.

Extracurricular laboratory: Synthetic route of 143591-61-1

The synthetic route of 3-Bromo-8-chloroimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Related Products of 143591-61-1, 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. 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 50;Tert-butyl 4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)imidazo[l,2- a]pyrazin-8-yl)piperazine-l-carboxylateStep 1: Tert-butyl 4-(3-bromoimidazo[l,2-a]pyrazin-8-yl)piperazine-l-carboxylate[0382] A mixture of tert-butyl piperazine-1-carboxylate (9.7 mmol) and 3- bromo-8-chloroimidazo[l,2-a]pyrazine (4.3 mmol) in 10 mL DMSO was heated to 100 0C for 45 minutes. The reaction mixture was cooled down to room temperature, and quenched with water. The mixture was rinsed into a seperatory funnel and extracted with ethyl acetate (3×50 mL). Combined organics were washed with water, brine and dried over Na2SO4, filtered and concentrated in vacuo to give tert-butyl 4-(3-bromoimidazo[l,2-a]pyrazin-8-yl)piperazine-l-carboxylate as tan solid (1.5 g).

The synthetic route of 3-Bromo-8-chloroimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; KAHRAMAN, Mehmet; SMITH, Nicholas, D.; BONNEFOUS, Celine; NOBLE, Stewart, A.; PAYNE, Joseph, E.; WO2010/88518; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Extended knowledge of 143591-61-1

Statistics shows that 3-Bromo-8-chloroimidazo[1,2-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 143591-61-1.

Related Products of 143591-61-1, These common heterocyclic compound, 143591-61-1, name is 3-Bromo-8-chloroimidazo[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.

3-Bromo-jV-isopropylimidazor 1 ,2-a1pyrazin-8-amine[00276] A neat mixture of 3-bromo-8-bromo/chloroimidazo[l,2-a]pyrazine (200 mg, 0.86 mmol) and isopropylamine (20 equivalents, 1.48 mL, 17.2 mmol) was stirred at 17O0C for 16hr in a sealed tube. After cooling down, the resulting mixture was partitioned between DCM (150 mL) and water (100 mL). The two layers were separated and the aqueous layer was extracted further with DCM (2 x 50 mL). The combined organic extracts were washed with brine until and dried over anhydrous MgSO4. Evaporation of the solvent afforded crude product (204 mg, 93%). LCMS RT = 1.23 min, MH+ 255.1 & 257.1. 1U NMR (CDCl3): 7.40-7.36 (2H, m), 7.30 (IH, d, J4.8), 5.72 (IH, br s), 4.42-4.22 (IH, br m), 1.27 (3H, s), 1.25 (3H, s).

Statistics shows that 3-Bromo-8-chloroimidazo[1,2-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 143591-61-1.

Brief introduction of 143591-61-1

The synthetic route of 143591-61-1 has been constantly updated, and we look forward to future research findings.

Application of 143591-61-1,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.

[00262] 5-(Trifluoromethyl)pyridin-3-amine (686 mg, 4.23 mmol) was dissolved in anhydrous DMF (24 rnL) and sodium hydride (231 mg, 5.77 mmol – 60% in mineral oil) added over 3 minutes before stirring the mixture at 200C under a nitrogen atmosphere for 20 minutes. 3-Bromo-8-bromo/chloroimidazo[l,2-a]pyrazine (895 mg, 3.85 mmol) was then added over 5 minutes and the mixture stirred at 200C under a nitrogen atmosphere for 16 hours. Water (170 mL) was added to the reaction mixture and the resulting precipitate was washed with water (125 mL) and then 40-60 petroleum ether (85 mL) to give 3-bromo-N-(5- (trifluoromethyl)pyridin-3-yl)imidazo[l,2-a]pyrazin-8-amine (871 mg, 63%) as an off-white solid. LCMS RT = 2.36 min, MH+ 359.9. 1U NMR (d6-DMSO): 9.42 (IH, s), 8.82 (IH, s), 8.62 (IH, d, J5.2), 8.01 (IH, d, J4.7), 7.89 (IH, s), 7.73 (IH, d, J4.8), 7.44 (IH, dd, J5.1, 0.9).

The synthetic route of 143591-61-1 has been constantly updated, and we look forward to future research findings.