Category: 1458-18-0

Related Products of 1458-18-0,Some common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, molecular formula is C6H5Cl2N3O2, 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 solution of methyl 3-amino-5, 6-dichloropyrazine-2-carboxylate (500 mg, 2.25 mol, 1 equiv) and 2- (tributylstannyl) -1, 3-oxazole (806.5 mg, 2.25 mol, 1.00 equiv) in 1, 4-dioxane (20 mL) were added LiCl (190.9 mg, 4.50 nMol, 2 equiv) , tricyclohexylphosphane (126.3 mg, 0.45 nMol, 0.2 equiv) and Pd 2 (dba) 3. CHCl 3 (466.2 mg, 0.45 nMol, 0.20 equiv) in portions at room temperature under nitrogen atmosphere. The resulted mixture was stirred for 4h at 140 under nitrogen atmosphere with microwave irritation. The resulted mixture was concentrated under reduced pressure. The residue was purified by Prep-TLC (CH 2Cl 2 /MeOH 20: 1) to afford methyl 3-amino-6-chloro-5- (1, 3-oxazol-2-yl) pyrazine-2-carboxylate (160 mg, 27.9%) as a yellow solid. LCMS: m/z (ESI) , [M+H] + = 255.1.

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; QI, Changhe; TSUI, Honchung; ZENG, Qingbei; YANG, Zhenfan; ZHANG, Xiaolin; (399 pag.)WO2020/35052; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, 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. HPLC of Formula: C6H5Cl2N3O2

Examples 54 and 55222.03 140.57[0266] Methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate, (3.2 gm, 0.0144 moles) and benzoyl chloride (7.03 gm, 0.05 moles) are combined in chloroform (50 mL) and pyridine (8 mL) is added. This mixture is stirred at 50C overnight. Additional portions of benzoyl chloride (3.5.0 gm, 0.025 moles) and pyridine (4 mL) are added and heating is continued at 65C overnight. The solution is cooled and methanol (25 mL) is added. After stirring for 30 minutes, the solvents are removed under reduced pressure. The solid residue is recrystallized from n-butanol.

The synthetic route of Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANUS BIOTHERAPEUTICS, INC.; LIPFORD, Grayson, B.; ZEPP, Charles, M.; WO2012/167046; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1458-18-0,Some common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, molecular formula is C6H5Cl2N3O2, 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.

Methyl 3-amino 5,6-dichloro-2-pyrazinecarboxylate (10 g, 45 mmol) was placed in a three-necked round bottom flask flushed with nitrogen, equipped with a bubbler and a gas condensor. The round bottomedflask and condensor were cooled to -80 C using a dry ice in acetone bath. Gaseous ammonia (500 mL) was condensed into the flask over a period of 1.5 h. Thereaction mixture was allowed to warm to reflux and maintained at reflux for a period of10 h. The ammonia then was allowed to evaporate from the flask (fume hood!) and the solid obtained was dried under high vacuum overnight to provide 3-amino-5,6-dichloro-2-pyrazinecarboxamide 4 (9.5 g, 100%) as solid,

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, its application will become more common.

Reference:
Article; Massey, Archna P.; Harley, William R.; Pasupuleti, Nagarekha; Gorin, Fredric A.; Nantz, Michael H.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 7; (2012); p. 2635 – 2639;,
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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1458-18-0

a) 3-Amino-6-bromo-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl esterTo a mixture of 3-amino-5,6-dichloro-pyrazine-2-carboxylic acid methyl ester [CAS 1458-18-0] and 3-amino-6-bromo-5-chloro-pyrazine-2-carboxylic acid methyl ester [CAS 14340-25-1] (799 mg, 3 mmol) in DMF was added 2-methoxy-ethylamine (0.31 ml, 3.6 mmol) and NEt3 (2.09 ml, 15 mmol) and the mixture was stirred at r.t. for 3.5 h. The reaction mixture was poured into water (150 ml) and extracted with toluene (2×150 ml). The organic layers were washed with half-saturated aq. sodium chloride, combined, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane/EtOAc 100:0 to 0:100%) to provide the title compound together with 3-amino-6-chloro-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl ester (about 1:1) as colorless solid. This mixture was used for the next step.HPLC: RtH4=0.77 min; ESIMS [M+H]+=305.1; (Cl-pyrazine: HPLC: RtH4=0.73 min; ESIMS [M+H]+=261.1).

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 1458-18-0.

Reference:
Patent; BADIGER, Sangamesh; CHEBROLU, Murali; HURTH, Konstanze; JACQUIER, Sebastien; LUEOEND, Rainer Martin; MACHAUER, Rainer; RUEEGER, Heinrich; TINTELNOT-BLOMLEY, Marina; VEENSTRA, Siem Jacob; VOEGTLE, Markus; US2012/184539; (2012); 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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

To a solution of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (0.444 g, 2.0 mmol) in tetrahydrofuran (5 mL)/water (10 mL)/toluene (20 mL) was added phenyl boronic acid (0.536 g, 4.4 mmol), sodium carbonate (0.699 g, 6.6 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.116 g, 0.10 mmol). The reaction was evacuated and purged with nitrogen several times before being refluxed for 6 h. The organic layer was separated and the aqueous layer extracted with toluene (3 x 20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and evaporated under reduced pressure to give methyl 3-amino-6-chloro-5-phenyl-2-pyrazinecarboxylate as a yellow solid (0.43 g, 82%).

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Biotron Limited; Gage, Peter William; Ewart, Gary Dinneen; Wilson, Lauren Elizabeth; Best, Wayne; Premkumar, Anita; US2015/313909; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1458-18-0, A common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, molecular formula is C6H5Cl2N3O2, 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.

PREPARATIVE EXAMPLES Preparative Exam ple1.A round bottomed flask was charged with methyl 6-amino 2,3-dichloro pyrazine 5-carboxylate (Aldrich, 25 g, 112.6 mmol), 2-S-ethyl piperazine (prepared as per Williams et al J. Med. Chem. 1996, 39, 1345, 83% active, 15.7 g, 112.7 mmol), cesium carbonate (100 g, 300 mmol) and 1 ,4 dioxane (400 ml). The flask was equipped with a reflux condenser and heated to8O0C. After 12 hours, the reaction was cooled, diluted with methylene chloride (~ 200 ml), and filtered through celite. The filtrate was washed once with water and then concentrated to an oil. The crude product was purified by silica gel chromatography using a methanol/ methylene chloride eluent (3% to 10% MeOH) to afford 30.8 g (91 %) of compound A3. MS, M+H = 300.

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/91428; (2006); A2;,
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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

General procedure: To a solution of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (1.0 eq.) in 2-propanol (5 mL/mmol), an appropriate primary or secondary amine(3-6 eq.) was added, and the reaction mixture wasrefluxed for 2 h.10) The solution was cooled to roomtemperature, concentrated under reduced pressure, andthe residue was purified by silica-gel column chromatography(Wako gel C-200, 30-40% ethyl acetate/n-hexane) to afford the series 1 intermediate (yield:32-95%). The regioselectivity of the nucleophilicsubstitution at the 5-position of the pyrazine ring wasconfirmed by an X-ray structural analysis (Fig. S1).

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Murai, Masatoshi; Habu, Sayako; Murakami, Sonomi; Ito, Takeshi; Miyoshi, Hideto; Bioscience, Biotechnology and Biochemistry; vol. 79; 7; (2015); p. 1061 – 1066;,
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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 1458-18-0

To a stirred mixture of methyl 3-amino-5, 6-dichloropyrazine-2-carboxylate (600 mg, 2.702 nMol, 1 equiv) and phenylboronic acid (336.09 mg, 2.756 nMol, 1.02 equiv) in dioxane (20 mL) were added K 3PO 4 (1147.23 mg, 5.405 nMol, 2 equiv) and Pd (dppf) Cl 2 (395.46 mg, 0.540 nMol, 0.2 equiv) in portions at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 3 h at 70 under nitrogen atmosphere. The resulting mixture was concentrated under reduced pressure. The residue was purified by Prep-TLC (PE/EtOAc 1: 1) to afford methyl 3-amino-6-chloro-5-phenylpyrazine-2-carboxylate (400 mg, 56.14%) as a yellow solid. LCMS: m/z (ESI) , [M+H] + = 264.3. 1H NMR (400 MHz, DMSO-d 6) delta 3.89 (3H, s) , 7.53 (3H, dd) , 7.61 (2H, s) , 7.71 -7.78 (2H, m)

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; QI, Changhe; TSUI, Honchung; ZENG, Qingbei; YANG, Zhenfan; ZHANG, Xiaolin; (399 pag.)WO2020/35052; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1458-18-0, 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 1458-18-0 as follows.

5,6-DICHLORO-3-HYDROXYPYRAZINE-2-CARBOXYLIC ACID (21). Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate (5.0 g, 23 mmol) was stirred in conc. sulfuric acid (140 mL) and cooled to 0 C. Sodium nitrite was added slowly, maintaining the temperature close to 0 C. After an additional 30 minutes at 0 C. the mixture was allowed to warm to ambient temperature and stirred for 3 hours. The mixture was poured into 500 g of ice, resulting in bubbling and foaming. After 30 minutes, the mixture was extracted 3 times with EtOAc. The combined organic extract was dried (MgSO4), filtered and concentrated. The yellow solid which was left was washed with water and air-dried, to leave 5.0 g of a yellow solid, m.p. 114-116 C. whose 13C-NMR spectrum was consistent with the methyl ester of the title compound. This solid (5.0 g) was treated with 1N NaOH (20 mL) and the mixture heated at 90 C. for 1.5 hours. After allowing to cool, the mixture was acidified with conc. HCl, then extracted 3 times with EtOAc. Drying (MgSO4), filtration and concentration afforded 0.48 g of a dark yellow solid, whose 1H-NMR and MS spectra were consistent with the title acid 21.

According to the analysis of related databases, 1458-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; US6355660; (2002); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1458-18-0, 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 1458-18-0 as follows.

The mixture of methyl 3-amino-5, 6-dichloropyrazine-2-carboxylate (0.5 g, 2.26 nMol) , 4, 4, 5, 5-tetramethyl-2- (5-methylfuran-2-yl) -1, 3, 2-dioxaborolane (0.71 g, 3.39 nMol) in dioxane (20 mL) was added Na 2CO 3 (0.94 g, 4.53 nMol) and Pd (dppf) Cl 2 (0.83 g, 1.13 nMol) at 100 . Then the mixture was stirred at this temperature for 2 h. LCMS showed the reaction was completed and purified with silica gel chromatography to give a desired product methyl 3-amino-6-chloro-5- (5-methylfuran-3-yl) pyrazine-2-carboxylate. LCMS: m/z (ESI) , [M+H] + = 268.4.

According to the analysis of related databases, 1458-18-0, the application of this compound in the production field has become more and more popular.