Category: 486424-37-7

Adding a certain compound to certain chemical reactions, such as: 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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 486424-37-7, name: 3-Amino-6-bromopyrazine-2-carboxylic acid

Example 5 : 3-Amino-6-(3-hydroxy-3-methyl-but-l-ynyl)-N-phenyl-pyrazine-2- carboxamide (Compound 11-81)SCHEME VSteps 1 to 2Compound 11-81METHOD E:Step 1: 3-Amino-6-bromo-N-phenylpyrazine-2-carboxamide[00151] A mixture of 3-amino-6-bromo-pyrazine-2-carboxylic acid (3.5 g, 16.05 mmol), l,l’-carbonyldiimidazole (5.205 g, 32.10 mmol), DIPEA (2.282 g, 3.075 mL, 17.66 mmol) and DMAP (98.04 mg, 0.8025 mmol) were combined in DMSO (131 mL) and stirred for 30 min. Aniline (1.495 g, 1.463 mL, 16.05 mmol) was then added and the resulting solution stirred at ambient tempaerture for 18 hours. After this time water was added and the product collected by filtration to give a brown powder (3.5 g, 74% Yield).1H NMR (400.0MHz, DMSO) delta 7.04 (1H, m), 7.29 (2H, m), 7.72 (4H, m), 8.36 (1H, s), 10.22 (NH2) ppm; MS (ES+) 295.

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; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; KNEGTEL, Ronald, Marcellus, Alphonsus; O’DONNELL, Michael; REAPER, Philip, Michael; WO2011/143419; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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 486424-37-7, Recommanded Product: 3-Amino-6-bromopyrazine-2-carboxylic acid

HATU (3.54 g, 9.36 mmol) was added to a solution containing 1.64 g (7.5 mmol) of 3-amino-6-bromopyrazine-2-carboxylic acid in 25 mL of DMF. The reaction was stirred for 5 minutes before adding 2.5 mL (22.5 mmol) of N-methylmorpholine and 1.68 g (9.36 mmol) of 4-morpholinopyridin-3-amine. The reaction mixture was stirred for 16 h then quenched with 10 mL of saturated NH4C1 solution and then 10 mL of water. The mixture was extracted with EtOAc three times; the combined organics were washed with brine and then dried over Na2S04. The solvent was then evaporated and the residue was chromatographed (0% to 20% CH3OH / dichloro methane) to afford compound Int lB-1 as a yellow solid.

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

Reference:
Patent; SILVERBACK THERAPEUTICS, INC.; THOMPSON, Peter Armstrong; EDRIS, Badreddin; COBURN, Craig Alan; BAUM, Peter Robert; ODEGARD, Valerie; (277 pag.)WO2018/227018; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 486424-37-7,Some common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, molecular formula is C5H4BrN3O2, 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.

CDI (2.23 g, 13.8 mmol) was added to a suspension of commercial 3-amino-6- bromopyrazine-2-carboxylic acid (2.00 g, 9.17 mmol) in DMF (20 ml). The reaction was stirred at RT for 16 h. The reaction mixture was cooled (0 C) then diluted with water (20 ml). The solid was collected by filtration then washed with the minimum volume of water and cooled (0 C) MeCN then dried under vacuum to afford the product as a yellow solid (2.23 g, 86%). 1H NMR (250 MHz, DMSO-cfe) delta 8.55 (s, 2H), 7.96 – 7.82 (m, 3H), 7.15 – 7.07 (dm, 1 H). LC/MS (System A, MeOH quench): m/z (ESI+) = 232 [Methyl ester M(79Br)H+], 234 [Methyl ester M(81Br)H+]), Rt = 0.87 min, UV purity = 95%.

The synthetic route of 486424-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); 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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C5H4BrN3O2

HATU (47.6 g) was added to a stirred solution of 1 ,2-phenylenediamine (13.54 g), 3-amino-6-bromopyrazine-2-carboxylic acid (26.0 g) and triethylamine (24.93 ml) in DMF (250 mL). The resulting solution was stirred at ambient temperature for 12 hours before the reaction mixture was added to water (250 ml). The resulting precipitate was collected by filtration, washed with water (250 ml) and dried in vacuo. This material was dissolved in acetic acid (200 ml) and heated to 9O0C for 4 hours. The reaction mixture was concentrated in vacuo, washed with diethylether. The ether washings were evaporated and triturated in hexane. There was thus obtained 3-(lH-benzimidazol-2-yl)-5-bromopyrazin-2-amine (5.Og); Mass Spectrum: M-H+ 290; RT 2.46 min. NMR Spectrum: (DMSOd6) 7.32 (m, 2H), 7.60 (d, IH), 7.78 (d, IH), 8.31 (s, IH), 13.2 (s, IH).

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; AstraZeneca AB; AstraZeneca UK Limited; WO2009/24825; (2009); 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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C5H4BrN3O2

Step 3 : 5-bromo-3-(6-methyl-lH-benzo[d]imidazol-2-yl)pyrazin-2-amine[00212] A mixture of 3-amino-6-bromo-pyrazine-2-carboxylic acid (2.5 g, 11.47 mmol) , 4- methylbenzene-l,2-diamine (1.401 g, 11.47 mmol), diethoxyphosphoryl-formonitrile (2.058 g, 1.871 mL, 12.62 mmol) and triethylamine (2.321 g, 3.197 mL, 22.94 mmol) was heated in DME (75.00 mL) at 17O0C in the microwave for 1 hour. The reaction mixture was diluted with EtOAc, filtered and washed with water and brine, dried over MgSO4 and concentrated to a brown solid. The mixture was slurried in DCM and treated with diethyl ether / petroleum ether. The resultant solid was washed with ether and dried to afford the product as an orange/brown solid (1.6g, 46% Yield). MS (ES+) 305

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; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-damien; DURRANT, Steven; KAY, David; O’DONNELL, Michael; KNEGTEL, Ronald; MACCORMICK, Somhairle; PINDER, Joanne; VIRANI, Anisa; YOUNG, Stephen; BINCH, Hayley; CLEVELAND, Thomas; FANNING, Lev, T.d.; HURLEY, Dennis; JOSHI, Pramod; SHETH, Urvi; SILINA, Alina; WO2010/54398; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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 486424-37-7, category: Pyrazines

The 3-(lH-benzimidazol-2-yl)-5-bromopyrazin-2-amine used as a starting material was prepared as follows :-etaATU (7.3 g) was added to a mixture of 3-amino-6-bromopyrazine-2-carboxylic acid (4 g), 1,2-phenylenediamine (2.07 g), triethylamine (3.8 ml) and DMF (40 ml) and the reaction mixture was stirred at ambient temperature for 1 hour. The resultant mixture was poured into aqueous sodium hydrogen carbonate solution and the resultant precipitate was isolated. The material so obtained was dissolved in acetic acid (20 ml) and heated to 900C for 3 hours. The resultant mixture was evaporated and the residue was triturated under methylene chloride. There was thus obtained 3-(lH-benzimidazol-2-yl)-5-bromopyrazin-2-amine (2.7 g); NMR Spectrum: (DMSOd6) 7.29 (m, 2eta), 7.59 (d, IH), 7.76 (d, IH), 8.28 (s, IH), 13.05 (s, IH); Mass Spectrum: M-HH+ 292; RT 2.34 min.

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; ASTRAZENECA AB; WO2009/7390; (2009); A2;,
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 486424-37-7 as follows. Application In Synthesis of 3-Amino-6-bromopyrazine-2-carboxylic acid

To the 3L into the reaction bottle 50.1g II, 2L methanol. 0 – 5 C lower, to the slowly dropping 133g 98.3% concentrated sulfuric acid, then completing, heating up to 40 C, instead on invitation 48h to raw material II basic reaction end. turns on lathe does methanol, 0 – 5 C lower, adding 200 ml methanol, 500g ice water mixture, wherein the aqueous solution of sodium bicarbonate to pH=6 – 7 adds by drops full and adjusted to. Filtering, the filter cake 45 C vacuum drying 12h, get 43.2g brown solid III, yield 80.1%

According to the analysis of related databases, 486424-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing Huawei Pharmaceutical Development Co., Ltd.; Bao Jinyuan; Huang Hui; Jiang Yuwei; Zhang Xiaoqing; (8 pag.)CN104496917; (2017); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 486424-37-7, 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 486424-37-7 as follows.

CDI (2.23 g, 13.8 mmol) was added to a suspension of 3-amino-6-bromopyrazine-2- carboxylic acid (2.00 g, 9.17 mmol) in DMF (20 ml). The reaction was stirred at RT for 16h. The reaction mixture was cooled (0 00) then diluted with water (20 ml). The solid wascollected by filtration then washed with the minimum volume of water and cooled (0 00)MeCN then dried under vacuum to afford the product as a yellow solid (2.23 g, 86%).1H NMR (250 MHz, DMSO-d6) O 8.58- 8.52 (m, 2H), 7.96-7.82 (m, 3H), 7.15- 7.07(m, 1H). LC/MS (System A, MeOH quench): mlz (ESl) = 232 [Methyl ester M(79Br)H], 234 [Methyl ester M(81Br)H]), R = 0.87 mi UV purity = 95%.

According to the analysis of related databases, 486424-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; MCCARTHY, Clive; (108 pag.)WO2019/77340; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 486424-37-7, 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 486424-37-7 as follows.

A mixture of 3-amino-6-bromopyrazine-2-carboxylic acid (3.90 mmol, 1.1 equiv), 3-(methylsulfonamido)phenylboronic acid (1.0 equiv), sodium carbonate (5.0 equiv) and Pd(PPh3)4 (10 mol %) were sequentially added in 30 mL 4:1 (v/v) degassed dioxane-water. The reddish brown mixture was stirred under Ar for 2 min at room temperature before heating to 88 C. for 2.5 hours. The mixture was slowly acidified by adding 30 mL of 10% citric acid until pH=4. The mixture was cooled to 25-30 C., diluted with 40 mL ethyl acetate, then 20 mL water and transferred to a separatory funnel. The aqueous layer was removed, extracted with ethyl acetate (3¡Á10 mL), the combined organic layers were washed with water (2¡Á20 mL) and brine (3¡Á20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to provide compound 181 as yellow solid which was washed with methylene chloride and used directly in the next step. ESI-MS m/z: 309.3 [M+H]+.

According to the analysis of related databases, 486424-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Intellikine LLC; Infinity Pharmaceuticals, Inc.; CASTRO, Alfredo C.; CHAN, Katrina; EVANS, Catherine A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LI, Liansheng; LIU, Tao; LIU, Yi; REN, Pingda; SNYDER, Daniel A.; TREMBLAY, Martin R.; US2013/267521; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 486424-37-7, A common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, molecular formula is C5H4BrN3O2, 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.

Triethyl amine (0.57 ML, 4.13 mmol) was added to a mixture of 3-AMINO-6-BROMO-2- pyrazinecarboxylic acid (0.30 g, 1.38 mmol; described in: Ellingson, R. C.; Henry, R. L. J. Am. Chem. Soc. 1949,2798-2800), 0- (BENZOTRIAZOL-1-YL)-NNN’, N’- tetramethyluroniumtetrafluoroborate (0.486 g, 1.51 mmol) and 1-hydroxybenzotriazole (0.204 g, 1.51 mmol) in N, N-DIMETHYLFORMAMIDE/ACETONITRILE, (1: 1,5 ML). After stirring for 0.5 h at room temperature, 2-(LH-PYRROL-L-YL)-L-ETANAMINE (0.182 g, 1.65 mmol) was added and the resulting mixture was stirred overnight at room temperature. Approximately, 10 ML water was added and a precipitation was formed. The precipitation was filtered and washed with water which gave 0.21 g (50% yield) of a light brown solid: MS (ESP) M/Z 310,312 (M++1). The solid (0.16 g, 0.516 mmol) from previous step was dissolved in tetrahydrofuran/water (5: 1,5 mL) together with [4- [ (4-methyl-l-piperazinyl) sulfonyl] phenyl] boronic acid (0.220 g, 0.77 mmol), sodium carbonate (0.164 g, 1.55 mmol) and Pd (dppf) CL2 (0.013 g, 1.5 nmmol). The resulting mixture was stirred at 70 C overnight (N2-atmosphere). The mixture was evaporated onto silica and purified on silica using toluene/acetonitrile, (1: 2 to 1: 4), as the eluent which afforded a yellow solid which was dried in vacuo at 40 C. The product was dissolved in a methylene chloride/methanol mixture, (9: 1), and hydrochloride acid in diethyl ether (0.28 mL, 1 M) was added. The precipitate was washed with diethyl ether and dried in vacuo to give 69 mg (23% yield) of the title compound : 1H NMR (DMSO-d6) 5 8.94 (s, 1 H), 8.90 (t, J = 6 Hz, 1 H), 8.43 (d, J = 8 Hz, 2 H), 7.82 (d, J = 8 Hz, 2 H), 6.79 (t, J = 2 HZ, 2 H), 6.01 (t, J = 2 HZ, 2 H), 4.12 (t, J = 7 Hz, 2 H), 3.83 (d, J = 12 Hz, 2 H), 3.63 (quart, J = 6 Hz, 2 H), 3.44 (d, J = 12 Hz, 2 H), 3.15 (m, 2 H), 2.73 (m, 5 H) ; 13C NMR (DMSO-d6) 8 165.8, 154.5, 144.8, 140.8, 135.9, 133.3, 127.9, 126.1, 124.6, 120.7, 107.8, 51.5, 47.6, 43.0, 41.8 ; MS (ESP) M/Z 470 (M++1).

The synthetic route of 486424-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/55009; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem