Category: 74290-67-8

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

Related Products 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 solution of 5-bromo-3-methyl-pyrazin-2-amine (1000 mg, 5.32 mmol), phenol (650 mg, 6.91 mmol), Cs2C03 (2600 mg, 7.98 mmol), Cul (203 mg, 1.06 mmol), and Nu,Nu-dimethylgly cine (110 mg, 1.06 mmol) in dioxane (5 mL) was degassed and heated to 90 C under N2 for 12 h. After cooling to room temperature, the mixture was diluted with EtOAc (100 mL) and water (100 mL) and the organic phase collected. The aqueous layer was extracted again with EtOAc (100 mL) and the combined organic layers were dried over anhydrous MgSC^ and concentrated to dryness. The residue was purified by flash column chromatography to give the title compound as a yellow oil (533 mg, 49.8% yield). MS (ESI): mass calcd. for CnHnN30, 201.1; m/z found, 202.1 [M+H]+.

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; JANSSEN PHARMACEUTICA NV; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CAI, Min; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; HAO, Baoyu; KREUTTER, Kevin; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; ZHU, Yaoping; ZHANG, Feihuang; ZHANG, Zheng; XIAO, Kun; (1000 pag.)WO2017/100668; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 74290-67-8,Some common heterocyclic compound, 74290-67-8, name is 2-Amino-5-bromo-3-methylpyrazine, molecular formula is C5H6BrN3, 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 2-amino-5-bromo-3-methylpyrazine (46.5 g, 247.3 mmol) in acetonitrile (450 mL) and THF (750 mL) was added DMAP (3 g, 24.7 mmol). The reaction mixture was stirred for 15 minutes before the addition of di-tert-butyl dicarbonate (242 g, 1 112.8 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated in vacuo, then diluted with EtOAc (750 mL) and washed with water (500 mL). The organic layers were dried over magnesium sulphate and concentrated in vacuo. The black tar was purified via flash chromatography, using a 10-15% EtOAc in heptane gradient. The resultant solid was triturated with IP A. The resulting white solid (the bis-tert-butoxycarbonyl derivative) was dissolved in methanol (3000 mL), then K2CO3 (61.25 g, 443 mmol) was added. The reaction mixture was stirred overnight at room temperature, then at 60C for 1 h, then allowed to cool and concentrated in vacuo. The residue was dissolved in DCM (1000 mL), then washed with water (2 x 1000 mL) and brine (500 mL). The organic layers were dried over magnesium sulphate, then concentrated in vacuo, to give the title compound (38 g, 80% pure by LCMS). LCMS (ES+) [M+H]+ 288.1 and 289.1 , RT 1.42 minutes (method 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-bromo-3-methylpyrazine, its application will become more common.

Reference:
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; HORSLEY, Helen Tracey; HUANG, Qiuya; REUBERSON, James Thomas; VANDERHOYDONCK, Bart; WO2014/96423; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 74290-67-8,Some common heterocyclic compound, 74290-67-8, name is 2-Amino-5-bromo-3-methylpyrazine, molecular formula is C5H6BrN3, 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 solution of 5-bromo-3-methyl-pyrazin-2-amine (1000 mg, 5.32 mmol), phenol (650 mg, 6.91 mmol), Cs 2CO 3 (2600 mg, 7.98 mmol), CuI (203 mg, 1.06 mmol), and N, N-dimethylglycine (110 mg, 1.06 mmol) in dioxane (5 mL) was degassed and heated to 90 under N 2 for 12 h. After cooling to room temperature, the mixture was diluted with EtOAc (100 mL) and water (100 mL) and the organic phase collected. The aqueous layer was extracted again with EtOAc (100 mL) and the combined organic layers were dried over anhydrous MgSO 4 and concentrated to dryness. The residue was purified by flash column chromatography to give the title compound as a yellow oil (533 mg, 49.8% yield). MS (ESI) : mass calcd. for C11H 11N 3O, 201.1 m/z found, 202.1 [M+H] +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-bromo-3-methylpyrazine, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CAI, Min; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; HAO, Baoyu; KREUTTER, Kevin D.; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; ZHU, Yaoping; ZHANG, Feihuang; ZHANG, Zheng; XIAO, Kun; (999 pag.)WO2018/103058; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application 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

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 74290-67-8, name is 2-Amino-5-bromo-3-methylpyrazine, A new synthetic method of this compound is introduced below., SDS of cas: 74290-67-8

Example 31 N-(3-((5-amino-6-methylpyrazin-2-yl)ethynyl)-2,4-difluorophenyl)-5-chloro-2-methylbenzenesulfonamide A mixture of 5-chloro-N-(3-ethynyl-2,4-difluorophenyl)-2-methylbenzenesulfonamide (100 mg), 5-bromo-3-methylpyrazin-2-amine (55 mg), dichlorobis(tricyclohexylphosphine)palladium(II) (14 mg), cesium carbonate (381 mg) and DMSO (2 mL) was stirred under microwave irradiation at 120 C. for 2 hr. After cooling to room temperature, the reaction mixture was filtered through celite, and the filtrate 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) and further purified by HPLC (C18, mobile phase: water/acetonitrile (0.1% TFA-containing system)). Fractions containing the object product were collected, neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate and concentrated to give a residue. The residue was washed with ethyl acetate/IPE/hexane to give the title compound (32 mg). 1H NMR (300 MHz, DMSO-d6) delta 2.29 (3H, s), 2.57 (3H, s), 6.87 (2H, s), 7.13-7.33 (2H, m), 7.47 (1H, d, J=8.1 Hz), 7.58-7.68 (2H, m), 8.04 (1H, s), 10.56 (1H, s).

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 of 74290-67-8, 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. 74290-67-8, name is 2-Amino-5-bromo-3-methylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-bromo-3-methylpyrazin-2-amine (400 mg, 2.127 mmol) in 1 ,4-dioxane (20 ml_) was added potassium carbonate (588 mg, 4.25 mmol), tert-butyl carbamate (748 mg, 6.38 mmol), N,N’-dimethyl-1 ,2-ethanediamine (37.5 mg, 0.425 mmol) and Cul (40.5 mg, 0.213 mmol). The reaction mixture was heated to 100 C and stirred for 16h. The reaction was allowed to cool to room temperature. The reaction mixture was quenched with water (100 ml_). The resulting solution was extracted with EtOAc (3 x 100 ml_) and the organic layers were combined, washed with brine (2 x 100 ml_), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford crude product as a brown solid (400 mg, 70 % pure, 58% yield). Used without further purification.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EVANS, Karen Anderson; HILFIKER, Mark A.; MARCUS, Andrew Peter; PLOTNIKOV, Nikolay Valeryevich; RALPH, Jeffrey Michael; (142 pag.)WO2019/193540; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 74290-67-8,Some common heterocyclic compound, 74290-67-8, name is 2-Amino-5-bromo-3-methylpyrazine, molecular formula is C5H6BrN3, 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 suspension of 5-bromo-3-methylpyrazin-2-amine (4.63g, 24.6 mmol) in iPrOH (30 ml) was added l-bromo-2,2-dimethoxypropane (3.66 ml, 27.1 mmol), pyridinium para-toluene sulfonic acid (0.62g, 2.5 mmol) and the mixture heated to 65C in a sealed tube for 36h. The reaction was diluted with DCM, washed with saturated sodium hydrogen carbonate solution, dried (Na2S04) and concentrated. Purification by flash column chromatography on silica gel (EtOAc: Hept 1:4-1: 1) afforded the titled product as a light yellow crystalline solid (3.96 g, 71%). MS (m/e): 226.1 (M+H+, Br)

The synthetic route of 74290-67-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GREEN, Luke; PINARD, Emmanuel; RATNI, Hasane; WILLIAMSON, Patrick; (95 pag.)WO2015/197503; (2015); 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. 74290-67-8, name is 2-Amino-5-bromo-3-methylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

Example 110 N-(3-((5-amino-6-methylpyrazin-2-yl)ethynyl)-2,4-difluorophenyl)-5-chloro-2-methoxypyridine-3-sulfonamide A mixture of 5-chloro-N-(3-ethynyl-2,4-difluorophenyl)-2-methoxypyridine-3-sulfonamide (108 mg), 2-amino-5-bromo-3-methylpyrazine (54 mg), dichlorobis(tricyclohexylphosphine)palladium(II) (11 mg), cesium carbonate (290 mg) and DMSO (2 mL) was stirred under microwave irradiation at 120 C. for 2 hr. After cooling to room temperature, the reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane) and further purified by HPLC (C18, mobile phase: water/acetonitrile (0.1% TFA-containing system)). Fractions containing the object product were collected, neutralized with a saturated aqueous sodium hydrogen carbonate solution and extracted 2 times 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 washed with ethyl acetate/IPE and dried under reduced pressure to give the title compound (63 mg). 1H NMR (300 MHz, DMSO-d6) delta 2.30 (3H, s), 3.93 (3H, s), 6.86 (2H, s), 7.10-7.23 (1H, m), 7.32 (1H, td, J=8.9, 6.0 Hz), 8.04 (1H, s), 8.06 (1H, d, J=2.5 Hz), 8.49 (1H, d, J=2.6 Hz), 10.46 (1H, s).

According to the analysis of related databases, 74290-67-8, the application of this compound in the production field has become more and more popular.

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

Application 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.

EXAMPLE 11 Sodium hydride (60% dispersion in mineral oil; 0.1 g) was added portionwise to a stirred solution of 2-amino-5-bromo-3-methylpyrazine (0.188 g) in 1,2-dimethoxyethane (DHE; 4 ml). After 5 minutes 5-dimethylamino-1-naphthalenesulphonyl chloride (0.3 g) was added, in a single portion, and the reaction was allowed to a stir for 18 hours. 2M Aqueous citric acid solution (10 ml) was added and the reaction was extracted with dichloromethane (3*25 ml). The combined extracts were dried (MgSO4) and evaporated to give a brown oil. The oil was purified by chromatography on silica gel, eluding with dichloromethane/diethyl ether (1:1) to give 5-dimethylamino-N-(5-bromo-3-methyl-2-pyrazinyl)-1-naphthalenesulphonamide as a cream solid (0.138 g, 33%), m.p. 171-172 C.; mass spectrum (+ve FAB, DMSO/methanol/NBA): 421 (M+H)+.

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; Zeneca Limited; US5861401; (1999); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem