Category: 486424-37-7

Synthetic Route 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.

A suspension of S-amino-beta-bromo-pyrazine^-carboxylic acid (0.5g, 2.3 mmol) and 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenylboronic acid (patent WO 2003076422, 1.28g, 4.6 mmol) in MeCN (20ml) was treated with K2CO3 (3.8g, 27.5 mmol) in H2O (5ml) under nitrogen at room temperature. The mixture was stirred for 10 min before adding bis(triphenylphosphine)palladium dichloride (0.08g, catalytic) and stirred at 9O0C for 3 hr. The cooled reaction mixture was dilute with H2O (20ml), basified to ph4, filtered to remove catalyst and evaporated. The residue dissolved in DCM (200ml), washed with brine, dried (MgSO4) and condensed. The solid residue was subjected to flash column chromatography on silica eluting gradient of hexane to (2:1 , v/v) ethyl acetate and hexane to give title compound (0.38g, 44%) as a yellow solid; LC/MS: Rt 2.78 (Method A) [M+H]+ 374.

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

Reference:
Patent; VERNALIS (R & D) LIMITED; WO2008/38010; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference 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

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: 3-Amino-6-bromopyrazine-2-carboxylic acid

-Amino-6-bromopyrazine-2-carboxylic acid (53.59 g, 0.229 mol) and 4-hydroxy-3-aminopyridine (33.64 g, 0.275 mol) were mixed in THF (500 mL) and triethyl amine (115.86 g, 1.145 mol) was added. The mixture was stirred at 25 for 10 min. The temperature was raised to 55 C. and T3P (218.90 g, 0.344 mol) was added. The mixture was stirred at 55 C. for 30 min. Water (150 mL) was added at 55 C. and the mixture was stirred for 2 h at 55 C. Solvents were distilled of until fractions at 55-80 C. was removed.Acetonitrile (500 mL) was added followed by water (350 mL) while maintaining the temperature at 75 C. The mixture was stirred for 2 h at 75 C. The solid was isolated by filtration. The solid was washed with water (250 mL) followed by acetonitrile (250 mL). The solid was dried under vacuum at 80 C. for 5 h to give the title compound (84.5%)1HNMR (400 MHz, DMSO-d6): 11.64 (s, 1H) 10.26 (s, 1H) 8.78 (s, 1H) 8.45 (s, 1H) 7.78 (s, 2H) 7.72 (d, 1H) 6.31 (d, 1H).MS (ESI+) m/z 310 [M+H]+

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; US2011/118275; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. category: Pyrazines

Block B can be prepared according to scheme 2 in FIG. 2. Referring to FIG. 2, the synthesis of Block B can be performed as described below. (0164) Intermediate 6 Block B [0029] To a solution of Intermediate 6 (6.0 g, 27.4 mmol) in DMSO (30 mL) was added CDI (8.9 g, 54.8 mmol), DIPEA (3.8 g, 30.1 mmol) and DMAP (0.17 g, 1.37 mmol). The solution was stirred at rt for 4 hours. Aniline (2.5 g, 27.4 mmol) was added and the mixture was stirred at rt overnight. Water was added and the formed solid was collected by filtration. The crude product was purified by silica-gel column to afford 2.5 g of Block B (31 %) as yellow solid. (0165) [0030] LC-MS (M+l): 293.2; 1H MR (400 MHz, DMSO-d6) 510.28 (s, 1H), 8.42 (s, 1H), 7.78 (d, J = 8.0 Hz, 2H), 7.74 (s, 2H), 7.36 (t, J = 8.0 Hz, 2H), 7.13 (t, J = 7.6 Hz, 1H) .

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

Reference:
Patent; MERRIMACK PHARMACEUTICALS, INC.; DRUMMOND, Dary| C.; GENG, Bolin; KIRPOTIN, Dmitri B.; TIPPARAJU, Suresh, K.; KOSHKARYEV, Alexander; ALKAN, Ozan; (142 pag.)WO2017/123588; (2017); 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. SDS of cas: 486424-37-7

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

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. name: 3-Amino-6-bromopyrazine-2-carboxylic acid

Step 1. Synthesis of tert-butyl (l-(2-(3-amino-6-bromopyrazine-2-carboxamido) pyridin- 3 -y l)piperidin-4-yl)carbamate In a 100 mL round-bottom flask equipped with a magnetic stirrer, a solution of 3-amino- 6-bromopyrazine-2-carboxylic acid (1.044 g, 4.79 mmol), tert- butyl (l-(2-aminopyridin-3- yl)piperidin-4-yl)carbamate (1.4 g, 4.79 mmol), DIPEA (2.091 mL, 11.97 mmol) and HATU (2.185 g, 5.75 mmol) in DMF (15 mL) was stirred at 25 C for 15 hr. The reaction mixture was quenched with 30 mL water and extracted with EtOAc (3 X 20 mL). The ethyl acetate wash was dried over Na2S04 and concentrated. The crude product was purified by silica gel chromatography using ethyl acetate and heptane which gave 3-amino-N-(3-(4-aminopiperidin-l- yl)pyridin-2-yl)-6-bromopyrazine-2-carboxamide (1.76 g, 3.57 mmol) in 74 % yield. LC-MS (acidic method): : ret.time= 1.17 min, M+H = 492.3.

The synthetic route of 3-Amino-6-bromopyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; LUZZIO, Michael Joseph; PAPILLON, Julien; VISSER, Michael Scott; (213 pag.)WO2016/20864; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. Safety of 3-Amino-6-bromopyrazine-2-carboxylic acid

Step 1. Synthesis of tert-butyl (l-(2-(3-amino-6-bromopyrazine-2-carboxamido)pyridin- 3-yl)-4-methylpiperidin-4-yl)carbamate. In a 100 mL round bottom flask equipped with a magnetic stirrer HBTU (2.23 gm, 5.87 mmol), 3-amino-6-bromopyrazine-2-carboxylic acid (1.17 gm, 5.39 mmol), and N-ethyl-N- isopropylpropan-2-amine (1.28 mL, 7.34 mmol) were allowed to stir in DMF (15 ml) for 15 minutes whereupon tert-butyl (l-(2-aminopyridin-3-yl)-4-methylpiperidin-4-yl)carbamate (1.5 gm, 4.9 mmol) was added in one portion. Reaction was allowed to stir for 16hr. Reaction was then poured into DMF and extracted thrice with 50 mL ethyl acetate. Organic extracts were combined and dried with brine followed by anhydrous sodium sulfate. The residue was purified by silica gel using gradient chromotography ethanol – ethyl acetate 0 -10% which yielded pure tert-butyl (l-(2-(3-amino-6-bromopyrazine-2-carboxamido)pyridin-3-yl)-4-methylpiperidin-4- yl)carbamate (1.86 gm, 67.5% yield) upon evaporation of fractions containing the desired product. LC-MS (Acidic method): ret.time= 1.17 min, M+H = 508.3.

The synthetic route of 3-Amino-6-bromopyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; LUZZIO, Michael Joseph; PAPILLON, Julien; VISSER, Michael Scott; (213 pag.)WO2016/20864; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products 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.

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%

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

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. COA of Formula: C5H4BrN3O2

Step 1: 3-Amino-6-bromo-pyrazine-2-carboxylic acid N?-acetyl-hydrazideHATU (3.4 g, 9.05 mmol) and triethylamine (1.2 g, 12.06 mmol) were added to a suspension of 2-Amino-S-bromopyrazine-3-carboxylic acid (1 .40g, 6.03 mmol) and acetohydrazide (0.44 g, 6.03 mmol) in DCM (100 ml) and the resultant solution was stirred at ambient temperature for 24 hr. The reaction was monitored by TLC. The reaction mixture was poured into water(200 ml) and the solid collected by filtration and dried under vacuum to afford 3-amino-6- bromo-pyrazine-2-carboxylic acid N?-acetyl-hydrazide;LCMS: Rt 0.57mins MS mlz 274.0 [M+H}+; Method 2minLowpHvol

The synthetic route of 3-Amino-6-bromopyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; (395 pag.)WO2015/162459; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route 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.

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 a2S04. The solvent was then evaporated and the residue was chromatographed (0% to 20% CH3OH / dichloromethane) to afford compound Int lB-1 as a yellow solid

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; SILVERBACK THERAPEUTICS, INC.; THOMPSON, Peter Armstrong; EDRIS, Badreddin; COBURN, Craig Alan; BAUM, Peter Robert; (372 pag.)WO2018/227023; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem