Tag: M.W=200-300

Related Products 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.

To 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 -20C 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, de-DMSO): delta = 8.64 (1 H, s), 8.00 (1 H, d), 7.66 (1 H, d2.54 (3H, 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; SIEMEISTER, Gerhard; BADER, Benjamin; WENGNER, Antje, Margret; MUMBERG, Dominik; KOPPITZ, Marcus; KLAR, Ulrich; KROEMER, Guido; VITALE, Ilio; JEMAA, Mohamed; WO2014/20041; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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.

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

Application of 957230-70-5, 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. 957230-70-5 name is 3,6-Dibromopyrazin-2-amine, 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.

Step 1: N’-(3,6-Dibromo-pyrazin-2-yl)-N,N-dimethylformamidine (D) A mixture of 3,6-dibromo-pyrazin-2-ylamine (15.37 g, 60.80 mmol) and N,N-dimethylformamide dimethyl acetal (10.1 mL, 76.00 mmol), suspended in ethanol (150 mL), is refluxed for 2 hours. The reaction mixture is evaporated in vacuo affording the title compound. 1H-NMR (400 MHz, CDCl3) delta(ppm) 3.20 (s, 3H), 3.21 (s, 3H), 7.93 (s, 1H), 8.48 (s, 1H). LCMS: Rt 3.81 min (99.1%), m/z (APCI) 307 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,6-Dibromopyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; WIGERINCK, Piet Tom Bert Paul; ANDREWS, Martin James Inglis; De WEER, Marc Maurice Germain; SABOURAULT, Nicholas Luc; KLUGE, Stefan Christian; US2011/118269; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 723286-79-1, A common heterocyclic compound, 723286-79-1, name is tert-Butyl 5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, molecular formula is C10H16N4O2, 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.

To a solution of compound A48-1 (1.29 g, 5.75 mmol) in dry THF (50 mL) was added a solution of 2.5 M n-BuLi in hexane (2.53 mL, 6.33 mmol) at -78 C. under argon. After 15 min ethyl formate (702 muL, 8.63 mmol) was added and the reaction mixture was stirred for 15 min at -78 C. Saturated aqueous NH4Cl (150 mL) was added and the mixture was extracted with CH2Cl2 (3¡Á100 mL). The combined organic layer was dried (Na2SO4) and evaporated to dryness to afford aldehyde A48-2 (1.21 g, 83%).

The synthetic route of 723286-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUENENTHAL GmbH; US2009/186899; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route 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.

6 8-dibromo-3-iodo-imidazo[1 ,2-a]pyrazineTo a stirred solution of 8.7 g (31.4 mmol) 6,8-dibromo-imidazo[1 ,2-a]pyrazine which was prepared according to a procedure described in the Journal of Medicinal Chemistry, 1984, vol. 27, No. 2, p. 206 – 212 in 210 ml_Nu,Nu-dimethylformamide was added 7.42 g N-iodopyrrolidin-2,5-dione in one portion at 23 C. After 18 hours of stirring at 60 C, the solvent was removed in vaccuo and the residue was taken up in dichloromethane 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 of the title compound.

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; BAYER PHARMA AKTIENGESELLSCHAFT; KLAR, Ulrich; KOPPITZ, Marcus; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; SCOTT, William; WO2011/151259; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 951626-95-2, name is Ethyl 4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate, 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 951626-95-2, Formula: C9H11N3O3

A solution of lithium hydroxide monohydrate (2.73 g, 65.0 mmol) in H20 (30.0 mL) was added to a suspension of ethyl 4-oxo-4,5 ,6,7-tetrahydropyrazolo [1,5 -a]pyrazine-2- carboxylate (2.72 g, 13.0 mmol) in THF (30 mL) and MeOH (30 mL) at 0 C. Then, the suspension was stirred at rt overnight. The solvents were removed. H20 (20 mL) wasadded. The clear solution was cooled to 0 C, conc. HC1 (5.42 mL, 65.0 mmol) was added to bring pH to 3. The suspension was stirred at 0 C for 2 h, filtered, and dried to give a white solid (2.2 g, 93%). LC-MS(ESI) m/z: 182.1 [M+H].

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; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 117719-17-2, 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. 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

Preparation of Intermediate I-03. A mixture of intermediate I-02 (360 mg, 1.35 mmol), indazole-4-boronic acid hydrochloride (600 mg, 2.97 mmol), K2CO3 (2 mL of saturated solution), PdCl2(dppf).DCM (112 mg, 0.135 mmol) in DME (5 mL) was heated under microwave irradiation for 10 min at 130 C. The reaction mixture was filtered through a celite pad, washing with DCM. The filtrate was dried over Na2SO4 and concentrated. The crude was purified by flash column chromatography (Isolute Si II 10 g cartridge) eluting with a gradient of DCM/MeOH (from 100% to 90:10) to yield 250 mg of the intermediate I-03 pure (Y: 62%).

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-3-morpholinopyrazin-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Centro Nacional De Investigaciones Oncologicas (CNIO); US2012/83492; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 25710-18-3,Some common heterocyclic compound, 25710-18-3, name is 2,3-Dichloropyrido[2,3-b]pyrazine, molecular formula is C7H3Cl2N3, 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.

A suspension of 2,3-dichloro-pyrido[2,3-b]pyrazine (200mg; lmmol; leq), ethane sulfonamide (109.1 mg, 1 mmol, 1 eq.), 7-methyl-l,5,7-triazabicyclo[4.4.0]dec-5-ene on polystyrene. hi (862 mg, 2.5 mmol, 2.5 eq.) and NaI (149.87 mg, lmmol, 1 eq.) in DMA (5 ml) is heated at 1000C in the microwave for 1 hour under high absorbance. HCl in dioxane (374.9 mul, 4M; 1.5 mmol, 1.5 eq.) then 3,5-dimethoxyaniline (765.8 mg, 5 mmol, 5 eq.) are added, and the resulting reaction mixture is heated at 1700C in the microwave for 30 min. The polymer is filtered off, washed with DMA, and the solvent evaporated under reduced pressure. The product was extracted withEtOAc, the organic layer is washed with brine and dried under MgSO4 them conecentrated to near dryness. The residue is purified by preparative HPLC to afford 69.4 mg (18 percent) of the title EPO compound as a parent. The parent (58.6 mg, 0.15 mmol, 1 eq.) is suspended in water (2 ml) then potassium hydroxide (300.9 mul, 0.50 M, 0.15 mmol, 1 eq.) is added and the mixture is lyophilised to afford 64 mg (99 percent) of the title compound as a yellow powder. IH NMR (DMSO- d6) delta 8.92 (s, IH), 8.34 (dd, J = 4.5, 1.7 Hz, IH), 7.79 (dd, J = 7.9, 1.7 Hz, IH), 7.31 (d, J = 2.3 Hz, 2H), 7.14 (dd, J = 7.9, 4.5 Hz, IH), 6.16 (t, J = 2.3 Hz, IH), 3.78 (s, 6H), 3.40 (q, J = 7.5 Hz, 2H), 1.15 (t, J = 7.5 Hz, 3H). HPLC (max plot) 99percent; Rt 2.87 min. LC/MS: (ES+): 390.3, (ES-): 388.3.

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

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/23186; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 58139-04-1, name is 2-Iodo-3-methoxypyrazine, 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 58139-04-1, Product Details of 58139-04-1

To a solution of 2-iodo-3-methoxypyrazine (22)9 (118 mg, 0.5 mmol) in THF (1 mL) was added isopropylmagnesium chloride (0.3 mL, 0.6 mmol, 2 M in THF) at 0 C. The mixture was stirred for exactly 7 min and a solution of 1,1?-bisindole-3,3?-dicarbaldehyde (14) (29 mg, 0.1 mmol) in THF (1 mL) was added dropwise. The reaction mixture was warmed to room temperature for 18 h and diluted with ethyl acetate (15 mL). The organic solution was washed with water (10 mL) and NH4Cl (10 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography using n-hexanes/ethyl acetate (1:1) as eluent to give diol 16 as a yellow oil (51 mg, 0.098 mmol, 98%) and an inconsequential mixture of diastereomers, which was used immediately in the next step. To a solution of 16 (51 mg, 0.098 mmol) in dichloromethane/acetonitrile (1:2, 5 mL) were added triethylsilane (28 mg, 38.4 muL, 0.24 mmol) and boron trifluoride diethyl etherate (34 mg, 29.6 muL, 0.24 mmol) at 0 C. The reaction mixture was stirred at 0 C for an additional 30 min and diluted with dichloromethane (15 mL). The solution was washed with NaHCO3 (satd, 10 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash column chromatography using ethyl acetate/methanol (19:1) as eluent to give the title compound as a yellow oil (40 mg, 0.084 mmol, 86%); numax (neat)/cm-1 3054, 2947, 2925, 2865, 1540, 1450, 1391, 1310, 1123, 1009, 740; deltaH (400 MHz, CDCl3) 8.05 (2H, d, J 2.8, 2¡ÁArH), 7.96 (2H, d, J 2.8, 2¡ÁArH), 7.77 (2H, d, J 7.4, 2¡ÁArH), 7.19-7.12 (4H, m, 4¡ÁArH), 7.18 (2H, s, 2¡ÁArH), 6.82 (2H, d, J 7.8, 2¡ÁArH), 4.31 (4H, d, J 4.2, 2¡ÁCH2), 3.99 (6H, s, 2¡ÁMe); deltaC (100 MHz, CDCl3) 158.8 (2¡ÁC), 146.1 (2¡ÁC), 138.9 (2¡ÁCH), 137.3 (2¡ÁC), 135.9 (2¡ÁCH), 126.6 (2¡ÁC), 126.3 (2¡ÁC), 123.3 (2¡ÁCH), 120.9 (2¡ÁCH), 119.9 (2¡ÁCH), 112.2 (2¡ÁC), 109.2 (2¡ÁCH), 53.7 (2¡ÁMe), 28.9 (2¡ÁCH2); m/z (ESI) 499 (65%, [M+Na]+), 376 (15), 311 (12), 261 (100); HRMS (ESI, [M+Na]+) found 499.1858. [C28H24N6NaO2]+ requires 499.1853.

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

Reference:
Article; Wang, Christy; Sperry, Jonathan; Tetrahedron; vol. 70; 21; (2014); p. 3430 – 3439;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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.

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