Category: 486424-37-7

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

METHOD 11; Example 305; Synthesis of tert-butyl l-(3-(3-amino-6-bromopyrazine- 2-carboxamido)pyridin-4-yl)prperidin-3-ylcarbamate [0242] A solution containing 1 eq each of tert-butyl l-(3-aminopyridin-4- yl)piperidin-3-ylcarbamate, S-amino-beta-bromopyrazine-l-carboxylic acid, HOAT and EDC in DMF, at a concentration of 0.5 M, was stirred for 60 hours. The solution was diluted with EtOAc and was washed with H2O (4x), NaCl(sat.), was dried over MgSO4, was filtered and the volatiles were removed in vacuo. After purification by silica gel chromatography (EtOAc eluant), tert-butyl l-(3-(3-amino-6-bromopyrazine-2- carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate was obtained (78%). LCMS (m/z): 492.2 (MH+); LC R, = 2.68 min.

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

Reference:
Patent; NOVARTIS VACCINES AND DIAGNOSTICS, INC.; WO2008/106692; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 486424-37-7, 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. 486424-37-7 name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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.

tert-Butyl (3-(3-amino-6-bromopyrazine-2-carboxamido)-2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)benzyl)(methyl)carbamate (9B) A stirring, room temperature solution of 3-amino-6-bromopyrazine-3-carboxylic acid (2.18 g, 10 mmol), tert-Butyl (3-amino-2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)benzyl)(methyl) carbamate (4.61 g, 12 mmol) and HOBt (0.68 g, 5 mmol) in DMSO (16 mL) was treated with neat EDAC (4.79 g, 25 mmol). After 3 hours the reaction mixture was treated with water (50 mL) yielding a goo. The reaction mixture liquid was decanted off and the goo was treated with additional portions of water (40 mL each), again decanting between treatments. The goo was then partitioned between EtOAc (200 mL) and water (50 mL). The resulting organic phase was washed sequentially with saturated aqueous NaHCO3, 1N HCl, and then saturated aqueous NaHCO3 once again. The organic phase was then dried over Na2SO4, filtered and concentrated under reduced pressure to give an oil. This oil was placed under high vacuum overnight to yield 4.97 g (85%) of desired product as an amber oil. LC/MS: (>95%) (weak M+H=585; stronger M+23=607).

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; Atrin Pharmaceuticals LLC; Breslin, Henry Joseph; Gilad, Oren; Sperl, Gerhard; Brown, Eric J.; Butler, Laura; (77 pag.)US2017/291911; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 486424-37-7, These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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 11 : 3-(lH-Benzimidazol-2-yl)-5-(3-pyridyloxy)pyrazin-2-amine (Compound 11-12)SCompound 11-12 METHOD K:Step 1: 3-Amino-iV-(2-aminophenyl)-6-bromopyrazine-2-carboxamide[00169] To a solution of 3-amino-6-bromopyrazine-2-carboxylic acid (140 g, 0.64 mol), o- phenylenediamine (70 g, 0.65 mol) and TBTU (247 g, 0.77 mol) in DMF (1.5 L) at 0 C was added drop wise DIPEA (166 g, 1.29 mol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into water and the resultant precipitate isolated by filtration and washed with water. The precipitate was dried at 50C to give the sub-title compound as a brown solid that wasused in the next step without further purification product (140 g, 70 % Yield). XH NMR (400 MHz, DMSO) delta 4.95 (br s, 2H), 6.59 (m, 1H), 6.79 (d, 1H), 6.95 (m, 1H), 7.30 (d, 1H), 7.70 (bs, 2H), 8.40 (s, 1H) and 9.65 (s, 1H) ppm; MS (ES+) 307.8.

Statistics shows that 3-Amino-6-bromopyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 486424-37-7.

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

Reference of 486424-37-7, These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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-Amino-6-bromo -N- (3,4- difluorobenzyl) pyrazine-2-carboxamide: A mixture of 1.51 g 3-amino-6-bromo-2-carboxylic acid (6.93 mM mole), 30 ml dimethylformamide, 1.23 ml 3,4-difluoro benzylamine (10.4 mmol) and 2.40 ml N, N- diisopropylethylamine (13.8 mmol) in combination and stirred together, the batch and then 2.89 g (7-azo BTA) -N, N, N ‘, N’- tetramethyluronium hexafluorophosphate (7.60 mmol) and stirred for two hours , was added 250 ml of ethyl acetate and 150 ml of water, filtered, the organic phase was washed with 150 ml aqueous sodium bicarbonate wash, 50 ml brine, dried over magnesium sulfate drained, purified by flash column chromatography (0-50 % ethyl acetate; n-hexane), to collect 0.899 g of yellow powder (38%).

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

Reference:
Patent; BIOGEN MA INC.; SUNESIS PHARMACEUTICALS, INC.; ARNDT, JOSEPH; CHAN, TIMOTHY; GUCKIAN, KEVIN; KUMARAVEL, GNANASAMBANDAM; LEE, WEN-CHERNG; LIN, EDWARD YIN-SHIANG; SCOTT, DANIEL; SUN, LIHONG; THOMAS, JERMAINE; VAN VLOTEN, KURT; WANG, DEPING; ZHANG, LEI; ERLANSON, DANIEL; (469 pag.)TWI525093; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 486424-37-7, These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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 containing 1.63 g (7.5 mmol) of 2-amino-5-bromopyrazine carboxylic acid in 25 mL of DMF was added 3.54 g (9.36 mmol) of HATU. The reaction mixture was allowed to stir for 15 minutes before the addition of 1.68 g (9.36 mmol) of 3-amino-4- morpholinopyridine and 2.5 mL (22.5 mmol) of N-methylmorpholine. The reaction was stirred for 16 h then quenched with a 10 mL of a saturated NaHCO, solution and extracted with EtOAc three times. The combined organic extracts were washed with brine and dried over Na2S04. Evaporation of the solvent and column chromatography (Si02; 10% CH3OH /DCM) provided Intermediate A as a yellow solid. 1H NMR (CD3OD) d 9.51 (s, 1H), 8.76 (s, 1H), 8.39 (d, J=5.4Hz, 1H), 7.94 (d, J=8. lHz, 2H), 7.39-7.27 (m, 8H), 5.10 (s, 2H), 3.81 (t, J=7.5Hz, 4H), 2.96 (t, J=7.5Hz, 4H). [M+H]+ = 568.1.

Statistics shows that 3-Amino-6-bromopyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 486424-37-7.

Reference:
Patent; SILVERBACK THERAPEUTICS, INC.; SMITH, Sean Wesley; COBURN, Craig Alan; BAUM, Peter Robert; DUBOSE, Robert Finley; (335 pag.)WO2019/227059; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. Recommanded Product: 486424-37-7

Step 3 : 5-Bromo-3-(6-methyl-lH-benzo [d] imidazol-2-yl)pyrazin-2-amine[00141] A mixture of 3-amino-6-bromo-pyrazine-2-carboxylic acid (5.52g, 25.32 mmol), 4-methylbenzene-l,2-diamine (3.09g, 25.32 mmol), diethoxyphosphorylformonitrile (4.54, 27.85 mmol) and triethylamine (7.06 mL, 50.64 mmol) in DME (30 mL) was heated in the microwave at 170C for 60 minutes. The mixture was diluted with ethyl acetate, washed with water followed by aqueous aHC03 then brine. After drying over MgSC^, the mixture was decolourised with charcoal and filtered through silica gel. After concentration, the mixture was filtered to give gold coloured crystals (4.005g, 52% Yield). MS (ES+) 305.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 486424-37-7, its application will become more common.

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

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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 486424-37-7

Triethylamine (0.48 mL, 3.44 mmol) was added to a mixture of 3-amino-6-bromo-2- pyrazinecarboxylic acid (0.25 g, 1.15 mmol; described in: Ellingson, R. C.; Henry, R. L. J. Am. Chem. Soc. 1949,2798-2800), 0- (BENZOTRIAZOL-1-YL)-NNN’, N’-TETRAMETHYLURONIUM tetrafluoroborate (0.405 g, 1.26 mmol) and 1-HYDROXYBENZOTRIAZOLE (0.17 g, 1.26 mmol) in N,N-dimethylformamide/acetonitrile, (1: 1, 5ML). After stirring for 0.5 h at room temperature, 3-methoxyaniline (0.15 ML, 1. 38 mmol) was added and the resulting mixture was stirred overnight at room temperature. Water (5-10 mL) was added and the precipitate was filtered off and washed with water to give 0.25 g (68% yield) of a yellow solid: MS (ESP) m/z 323,325 (M++1).

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 486424-37-7.

Reference:
Patent; ASTRAZENECA AB; WO2004/55006; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 486424-37-7, The chemical industry reduces the impact on the environment during synthesis 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life.

To 3-amino-6-bromo-pyrazine-2-carboxylic acid (5.0g, 22.9mmol), HOBt (3.867g, 22.9mmol), EDCI (9.15g, 47.62mmol) and NEt3 (8mL, 58mmol) in DMF (80mL) was added C-((R)-1-Isopropyl-piperidin-3-yl)-methylamine (2.98g, 19.08mmol) in DMF (20mL). The reaction mixture was heated at 45oC for 18h before the volume reduced by half in vacuo and water was added. The aqueous phase was extracted with EtOAc and the combined organic phase was washed with sat. NaHCO3, brine, dried (MgSO4) and the solvent was removed in vacuo. The residue was purified by column chromatography (NEt3:THF 5:95) to give, after removal of the solvent in vacuo, the title compound: RT = 1.92 min; m/z (ES+) = 356.1, 358.1 [M+H]+.

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-Amino-6-bromopyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hanrahan, Patrick; Bell, James; Bottomley, Gillian; Bradley, Stuart; Clarke, Phillip; Curtis, Eleanor; Davis, Susan; Dawson, Graham; Horswill, James; Keily, John; Moore, Gary; Rasamison, Chrystelle; Bloxham, Jason; Bioorganic and Medicinal Chemistry Letters; vol. 22; 6; (2012); p. 2271 – 2278;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. HPLC of Formula: C5H4BrN3O2

A solution of 3-amino-6-bromo-pyrazine-2-carboxylic acid (0.62 g, 2.8 mmol), HATU (1.3 g, 3.4 mmol) and di-isopropylethylamine (1.72 ml, 3.5 mmol) in DMF (20 ml) is stirred at room temperature for 5 minutes. N-Methoxy-N-methylamine hydrochloride (0.33 g, 3.4 mmol) is added and the reaction is stirred at room temperature for 2 hours. The solvent is concentrated in vacuo and the residue dissolved in EtOAc (30 ml), and washed with sat. aq. NaHCO3 (20 ml), 0.1N HCl (20 ml), dried (MgSO4) and concentrated in vacuo to yield a brown oil. Purification by flash chromatography (SiO2, 30% EtOAc in iso-hexane) yields 3-amino-6-bromo-pyrazine-2-carboxylic acid methoxy-methyl-amide as a yellow solid [M+H]+ 261.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 486424-37-7, its application will become more common.

Reference:
Patent; BRUCE, Ian; BUDD, Emma; EDWARDS, Lee; HOWSHAM, Catherine; US2009/239847; (2009); 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, name: 3-Amino-6-bromopyrazine-2-carboxylic acid

Dichlorobis(triphenylphosphine)palladium (H) (0.04 g) was added to a solution of 1 – { 2-[2-methoxy-4-(4,4,5,5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-yl)phenoxy]ethyl Jpyrrolidine (1.26 g), 3-amino-6-bromopyrazine-2-carboxylic acid (0.844 g) and 2M aqueous sodium carbonate solution (2.4 ml) in a 2:7:3:2 mixture of DMF:dimethoxyethane:water:ethanol (30 ml). The reaction mixture was heated to 1600C for 20 minutes in a IOOW microwave oven. The mixture was cooled to ambient temperature and diluted with methanol. The resultant mixture was added to an SCX ion exchange column which was eluted with methanol, followed by 2M methanolic ammonia solution. There was thus obtained 3-amino- 6-[3-methoxy-4-(2-pyrrolidin-l-ylethoxy)phenyl]pyrazine-2-carboxylic acid (1.2 g); Mass Spectrum: M+H* 359; RT 0.79 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