Month: September 2021

Synthetic Route of 6905-47-1, A common heterocyclic compound, 6905-47-1, name is 2-Amino-6-methoxypyrazine, molecular formula is C5H7N3O, 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 of 6-methoxypyrazin-2-amine (0.5 g, 4.0 mmol) in CHCI3 (25 mL) was added NCS (533 mg, 4.0 mmol). The reaction mixture was stirred at 40C for 12 h. The mixture was concentrated to give a residue. The residue was purified by column chromatography (Si02) to give 5-chloro-6-methoxypyrazin-2-amine (95 mg, 14.9% yield) as a yellow solid. NMR (400MHz, CHLOROF ORM-f) delta 7.32 (s, 1H), 4.42 (s, 2H), 3.96 (s, 3H).

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; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (214 pag.)WO2019/94641; (2019); A1;,
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 14508-49-7 as follows. Application In Synthesis of 2-Chloropyrazine

A mixture of 2-hydrazinopyrazine (820 mg, 7.45 mmol), prepared from 2-chloropyrazine and hydrazine using a procedure analogous to that described in the literature (P. J. Nelson and K. T. Potts, J. Org. Chem. 1962, 27, 3243, except that the crude product was extracted into 10% methanol/dichloromethane and filtered, and the filtrate was concentrated and purified by flash chromatography on silica gel, eluting with 100% ethyl acetate followed by 10% methanol in dichloromethane), TFA (2.55 g, 22.4 mmol), and polyphosphoric acid (10 mL) was heated to 140 C. with stirring for 18 h. The solution was added to ice and neutralized by the addition of ammonium hydroxide. The aqueous solution was extracted with ethyl acetate (3×), washed with brine, and dried over anhydrous magnesium sulfate. Concentration followed by flash chromatography (silica gel, 1:1 hexane:ethyl acetate, then 100% ethyl acetate) afforded the title compound as a solid (861 mg). 1H NMR (500 MHz, CDCl3) delta 8.17-8.20 (m, 2H), 9.54 (s, 1H). LC/MS (M+1) 189.

According to the analysis of related databases, 14508-49-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Corp.; Edmondson, Scott D.; Fisher, Michael H.; Kim, Dooseop; Maccoss, Malcolm; Parmee, Emma R.; Weber, Ann E.; Xu, Jinyou; US2015/359793; (2015); 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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H7N3O2

Example 81; Synthesis of (3,5-bis-trifluoromethyl-benzyl)- [3-(cycIopentylmethyl-ethyl-amino)- pyrazin-2-ylmethyl]-carbamic acid methyl ester; Step (i): Synthesis of 3-bromo-pyrazine-2-carboxylic acid methyl ester; Copper bromide (1.36 g, 6.1 mmol) and .pound.-butyl nitrite (0.78 g, 7.6 mmol) were added to a 50 mL round bottom flask along with acetonitrile (2 niL), and this mixture was heated at 60 0C for 5 min. After this time, 3-amino-pyrazine-2-carboxylic acid methyl ester (0.8 g, 5.09 mmol) was added portion- wise, with stirring, and stirring was continued at the same temperature for another 10 min. The reaction mixture was then cooled to RT, poured into 100 mL of dilute HCL (2N), and then extracted with diethyl ether (3 x 50 mL). The combined organic layer was washed with dilute HCl, dried over sodium sulfate, and then concentrated under vacuum to afford the title compound (0.139 g), yield: 12 percent.1H NMR (CDCl3, 400 MHz): d 8.58 (m, 2H), 4.04 (s, 3H)) ; m/z (CI-MS) 217 (M+) ; IR (neat, cm-1): 3385, 2955, 1742

The synthetic route of 16298-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; BARUAH, Anima; DE, Dibyendu; KHANNA, Ish Kumar; PILLARISETTI, Sivaram; MAITRA, Santanu; ALEXANDER, Christopher, W.; SREENU, Jennepalli; DAGER, Indu; WO2006/73973; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

356783-16-9, 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. 356783-16-9, name is 3,6-Dichloropyrazine-2-carbonitrile belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

REFERENTIAL EXAMPLE II-11 In 15 ml of dimethylformamide was dissolved 1.5 g of 3,6-dichloro-2-pyrazinecarbonitrile. After adding 1.2 g of 4-methoxyphenol and 1.8 g of potassium carbonate, the mixture thus obtained was stirred at room temperature for 30 minutes. A mixture of 20 mL of ethyl acetate and 60 mL of water was added to the reaction mixture, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=5:1] to obtain 2.1 g of 6-chloro-3-(4-methoxyphenoxy)-2-pyrazinecarbonitrile as a yellow-colored solid product. R (KBr) cm-1: 2236 H-NMR (CDCl3) delta: 3.83(3H,s), 6.95(2H,d,J=9.2 Hz), 7.11(2H,d,J=9.2 Hz), 8.26(1H,s)

The synthetic route of 356783-16-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Toyama Chemical Co., Ltd.; US2003/130213; (2003); 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. 126069-70-3, name is 2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H8F3N3

2-Fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoic acid 1a (500 mg, 1.68 mmol) was dissolved in 10 mL of N,N-dimethylformamide, followed by addition of O-(1-benzotriazolyl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (830 mg, 2.52 mmol), 2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-c]pyrazine 12c (384 mg, 2 mmol) and N,N-diisopropylethylamine (1 mL, 5 mmol). After stirring for 12 hours, the resulting residue was purified by silica gel column chromatography with elution system A to obtain 4-[[4-fluoro-3-[2-(trifluoromethyl)-6,8-dihydro-5H-imidazo[1,2-c]pyrazine-7-carbonyl]phenyl]methyl]-2H-phthalazin-1-one 12 (200 mg, yield 25.0%) as a white solid. MS m/z (ESI): 472.1[M+1] 1H NMR (400 MHz, CDCl3): delta 10.29 (br. s, 1H), 8.47 (m, 1H), 7.80 (m, 3H), 7.37 (m, 2H), 7.25 (m, 1H), 6.50 (m, 1H), 4.67 (s, 2H), 4.28 (m, 2H), 4.14 (m, 2H), 3.73 (m, 2H)

According to the analysis of related databases, 126069-70-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JIANGSU HANSOH PHARMACEUTICAL CO., LTD.; Tang, Peng Cho; Li, Xin; Li, Xiangqin; Chen, Yang; Wang, Bin; Zhu, Zhe; US2013/131068; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 369638-68-6, A common heterocyclic compound, 369638-68-6, name is tert-Butyl (5-methylpyrazin-2-yl)carbamate, molecular formula is C10H15N3O2, 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.

Step 2: To a solution of (5-methyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (from above and from example 21, step 1, 12.9 g, 61.6 mmol) and AIBN (10.1 g, 61 mmol) in CCl4 (100 mL) was added NBS (11 g, 61.6 mmol) and the reaction mixture was stirred at 100 C. for 4 h. The reaction mixture was filtered, washed with CH2Cl2 and concentrated in vacuo. Purification by chromatography (silica, 4:5:1 CH2Cl2:hexanes:ethyl acetate) with repurification of mixed fractions by chromatography (silica, 4:5:1 CH2Cl2:hexanes:ethyl acetate) afforded a total of (5-bromomethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (13.6 g, 77%): 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.57 (s, 9H) 4.55 (s, 2H) 8.15 (s, 1H) 8.34 (d, J=1.51 Hz, 1H) 9.28 (d, J=1.51 Hz, 1H).

The synthetic route of 369638-68-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brotherton-Pleiss, Christine E.; Walker, Keith A. M.; US2012/149718; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, molecular formula is C6H6N2O, 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: C6H6N2O

General procedure: Catalyst (0.1mol %) and KOH (1mmol) were dissolved in 2-propanol (4mL). To this solution, substrate (1mmol) was added and the mixture was refluxed (82C). The progress of the reaction was monitored by GC at regular intervals. After the completion of the reaction, the reaction mixture was cooled to room temperature and filtered through silica gel or alumina bed, and eluted using 50% ethyl acetate-hexane mixture. The eluted solution was reduced and analyzed by GC and/or GCMS.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22047-25-2, its application will become more common.

Reference:
Article; Sathishkumar, Pushpanathan N.; Raveendran, Neethi; Bhuvanesh, Nattamai S.P.; Karvembu, Ramasamy; Journal of Organometallic Chemistry; vol. 876; (2018); p. 57 – 65;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-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. Recommanded Product: 5521-55-1

A boron trifluoride-diethyl ether complex (91.7 IL) was added dropwise to a suspension of 2-methylpyrazine-5-carboxylic acid (1 g) and tert-butyl 2,2,2-trichloroacetimidate (4.75 g) in tetrahydrofuran (20 mL) under ice-cooling. The reaction solution was heated to room temperature and stirred for two hours. A saturated sodium chloride solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the insoluble matter was separated by filtration. The filtrate was concentrated and purified by silica gel column chromatography to obtain the title compound (1.4 g).1H-NMR (CDCl3) delta (ppm): 1.65 (s, 9H), 2.65 (s, 3H), 8.57 (d, J=1.2 Hz, 1H), 9.10 (d, J=1.6 Hz, 1H).

The synthetic route of 5-Methylpyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; US2010/93999; (2010); 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. 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C6H6N2O2

General procedure: To the dipeptide salt (7 or 11, 1 mmol) in Schemes 2 and 3 wasadded a solution of 7 N NH3 in CH3OH (10 mL) and reaction mixturewas stirred for 10 min at 0 C. The solvent was evaporatedunder reduced pressure to afford free peptides, which was dissolvedin DMF (4 mL) and cooled to 4 C. To this reaction mixturerequisite carboxylic acid (1 mmol), DIC (1.1 mmol) and HOBt(1.1 mmol) was added and stirring continued at 4 C for 36 h. Thesolvent was removed under reduced pressure and the resultingresidue purified by column chromatography over neutral alumina using CHCl3/CH3OH (4:1) as eluant to afford desired peptides.The peptides were checked for their homogeneity on aShimadzu SPD-M20A HPLC system using a Supelcosil LC-8(25 cm 4.6 mm ID) column. The peptides were analyzed by usingan isocratic solvent system of CH3CN-H2O-TFA (70:30:0.8%) usinga SUPELCOSIL C-18 column with a flow rate of 1 mL/min

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:
Article; Meena, Chhuttan L.; Thakur, Avinash; Nandekar, Prajwal P.; Sangamwar, Abhay T.; Sharma, Shyam S.; Jain, Rahul; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5641 – 5653;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, 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. Recommanded Product: 2-Bromo-5-iodopyrazine

2-Bromo-5-iodopyrazine [CAS RN: 622392-04-5] (3.50 g, 12.3 mmol, 1.0 eq),4,4,5,5-tetramethyl-2-(prop-1 -en-2-yl)-1 ,3,2-dioxaborolane [CAS RN: 126726-62-3] (3.10 g, 18.4 mmo[, 1.5 eq), Pd(dppf)C[2.CH2C[2 (502 mg, 0.61 mmo[, 0.05 eq) and cesium carbonate (12.0 g, 36.9 mmo[, 3.0 eq) were dissolved in 130 mL dioxane/water (5/1). The reaction mixture was heated to 90C for 2 h. On cooling, the reaction mixture was partitioned between water anddichloromethane. The organic phase was washed with brine and the phases were separated by the use of a Whatman filter. The volatile components were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 100 g SNAP cartridge: hexane -> hexane/ethyl acetate 9/1) to give 600 mg (25% yield of theory) of the title compound in a round 50% purity(UPLC-area%). The impurity was identified as 2,5-di(prop-1-en-2-yl)pyrazine, that was not expected to interfere in the subsequent reaction step. The material obtained was used without further purification.UPLC-MS (Method 4): R = 1.18 mm; MS (ESI0): m/z = 199 [M].

The synthetic route of 2-Bromo-5-iodopyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem