Month: February 2021

Application of 6164-79-0, 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. 6164-79-0 name is Methyl 2-pyrazinecarboxylate, 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.

Example 1D; Methyl 4-oxy-2-pyrazinecarboxylate; Methyl 2-pyrazinecarboxylate (Pyrazine Specialists, 10.04 g, 72.2 mmol) was suspended in 1,2-dichloroethane (100 mL). To the reaction mixture was added mCPBA (32.35 g, 77%, 144 mmol). The reaction was stirred at 60 C. for 16 h. The reaction was then allowed to cool to ambient temperature and diluted with CH2Cl2 (300 mL). The precipitate was filtered off and washed with additional CH2Cl2 (3¡Á35 mL). The filtrates were combined, dried over K2CO3, filtered and concentrated under vacuum. The residue was suspended in hexane (50 mL). The title compound was isolated by filtration, washed with additional hexane (2¡Á50 mL) to afford a slightly yellow solid (7.22 g, 64%). 1H NMR (DMSO-d6, 300 MHz) delta ppm 3.91 (s, 3H), 8.54 (dd, J=4.07, 1.69 Hz, 1H), 8.64-8.67 (m, 2H). MS (DCI/NH3) m/z 155 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-pyrazinecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Abbott Laboratories; US2009/281118; (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. 5049-61-6, name is Pyrazin-2-amine, A new synthetic method of this compound is introduced below., COA of Formula: C4H5N3

2-Pyrazinamine (9.51 g, 100 mmol) was dissolved in ethanol (300 ml) and 2-bromo- 1 ,1-bis(ethyloxy)ethane (21.06 ml, 140 mmol) was added. 48% hydrobromic acid (33.3 ml) was added and the mixture heated at reflux for 24 hr. The solution was concentrated in vacuo to a crude solid that was basified with 10% ammonia-ice (300ml). The solution was extracted in to ethyl acetate (3 x 300ml), the combined extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford a crude solid, (4.76g). The solid was purified by flash chromatography (Biotage SP4, 40+M, eluting with a 0-100% [25% 2M ammonmia/methanol in dichloromethane] in dichloromethane gradient) to afford imidazo[1 ,2-a]pyrazine (2.86 g, 24.01 mmol, 24.01 % yield).).1H NMR (CDCI3, 400 MHZ) d 9.11 (s, 1 H), 8.10 (d, 1 H, J = 4.8 Hz, 7.88 (d, 1 H. 4.8 Hz, 7.83 (s, 1 H), 7.71 (s, 1 H)

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; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALL, Ian David; WALTER, Daryl Simon; WO2010/125101; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

109-08-0, name is 2-Methylpyrazine, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 109-08-0

To a solution of 2- methylpyrazine (20.0 g, 212 mmol) in 1,4-dioxane (140 ml) was added ethyl 2-oxoacetate (56.4 g, 276 mmol) and diacetoxyiron (0.99 g, 6.4 mmol) under N2. The reaction was heated at 140¡ãC for 48 h. The mixture was concentrated under reduced pressure. The residue was purified by FCC (0 – 10percent EtOAc / petroleum ether) to give the title compound. Y = 30 percent. .H NMR (400 MHz, chloroform-;/) delta 8.54 – 8.48 (m, 3H), 4.70 – 4.64 (m, 1H), 4.26 (q, J= 8 Hz, 2H), 3.38 – 3.33 (m, 1H), 3.25 – 3.19 (m, 1H), 1.26 (t, J= 7 Hz, 3H).

The synthetic route of 109-08-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NODTHERA LIMITED; BOCK, Mark G.; WATT, Alan Paul; PORTER, Roderick Alan; HARRISON, David; (229 pag.)WO2019/25467; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 63744-22-9,Some common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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.

6,8-dibromo-imidazo[1 ,2-a]pyrazine which was prepared according to a procedure described in the Journal of Medicinal Chemistry, 1984, vol. 27, No. 2, p. 206 – 212 in 2.9 L methanol at -20 C was dropwise added a solution of 225 g sodium methanethiolate in 800 mL water. After stirring overnight, the clear solution was poured into 30 L water, the precipitate was filtered, washed with water and dried in vaccuo to yield 301 g (70%) of the title compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6,8-Dibromoimidazo[1,2-a]pyrazine, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KLAR, Ulrich; KOPPITZ, Marcus; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; SCOTT, William; WO2011/151259; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 123-32-0, name is 2,5-Dimethylpyrazine, 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 123-32-0, Quality Control of 2,5-Dimethylpyrazine

Preparation of 3,6-dimethyl-2- (4-chloro) benzoyl pyrazine, comprising the steps of:(1) 2,5-dimethyl pyrazine take 0.2mmol, 4- chloro-benzoyl formate 0.4mmol, 0.02 mmol silver phosphate, potassium persulfate 5mL reaction tube was placed 0.4mmol, 1.4mL was added dichloro methane, 0.6 mL of distilled water was added, and the mixture was placed in an oil bath at 40 heated, reaction 24h, cooled to room temperature to obtain a reaction solution;(2) The step (1) the resulting reaction mixture was directly concentrated to give a concentrate, the concentrate with ethyl acetate / petroleum ether = 1/2 (v / v) as the developing solvent, separation by thin layer chromatography to give 46 mg desired product in 94% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,5-Dimethylpyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Henan Agricultural University; Wu Zhiyong; Zhao Mingqin; Li Yuan; (10 pag.)CN108101856; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 939412-86-9, 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of (l^S^-S-^ethoxycarbony^^^^-trimethylcyclopentanecarboxylic acid (4.93 g, 23.01 mmol) and TEA (9.62 mL, 69.0 mmol) and HATU (13.12 g, 34.5 mmol) in DCM (100 mL) was stirred at 12 C for 30 min. (3-chloropyrazin-2-yl) methanamine hydrochloride (4.97 g, 27.6 mmol) was added and the mixture was stirred at 12 C for overnight. The reaction was complete detected by LC-MS. The mixture was added DCM (100 mL) and washed and brine. The organic layer was dried over Na2S04, purified with silica gel to give the title compound. XH NMR (400MHz, CDC13): delta 8.46 (d, J=2.3 Hz, 1H), 8.34 (s, 1H), 6.70 (br. s., 1H), 4.81 – 4.66 (m, 2H), 3.69 (s, 3H), 2.74 (t, J=9.2 Hz, 1H), 2.65 (dt, J=6.8, 12.6 Hz, 1H), 2.34 – 2.22 (m, 1H), 1.91 – 1.80 (m, 1H), 1.54 (ddd, 3=4.1, 9.6, 13.7 Hz, 1H), 1.32 (s, 3H), 1.25 (s, 3H), 0.81 (s, 3H).

The synthetic route of (3-Chloropyrazin-2-yl)methanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph, A.; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; LIU, Shilan; (85 pag.)WO2016/109219; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 122-05-4,Some common heterocyclic compound, 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, molecular formula is C6H4N2O4, 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.

After dissolving 76.8 mmol of I2 in 70 ml of pyridine, was added to a 250 ml three-necked flask and heated to 100 C under a nitrogen atmosphere, A solution of 120 ml of pyridine (completed in 4 hours) containing 27.41 mmol of 2,5-dicarboxylic acid pyrazine was slowly added dropwise, After completion of the dropwise addition, heating was continued for 2 hours, cooled, filtered and washed with 50 ml of ether to give a brown powder solid. The powder solids were then placed in a round bottom flask and 150 ml of methanol was added, heated to reflux for 1 h, cooled, filtered, Followed by washing with 40 ml of methanol and 40 ml of diethyl ether to give a brown powder as an intermediate 2,5-dicarboxylic acid pyrazine pyridinium iodide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Pyrazine-2,5-dicarboxylic acid, its application will become more common.

Reference:
Patent; Zhengzhou University of Light Industry; LI, XILI; ZHOU, LIMING; LI, CAIFENG; GAO, LIJUN; FANG, SHAOMING; (15 pag.)CN103896972; (2016); B;,
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. 88625-24-5, name is 5-Chloropyrazine-2-carbaldehyde, A new synthetic method of this compound is introduced below., category: Pyrazines

4,4-Difluoropiperidine hydrochloride [CAS RN: 144230-52-4] (495 mg, 3.14 mmol,1.6 eq), 5-chloropyrazine-2-carbaldehyde [CAS RN: 88625-24-5] (280 mg,3.14 mmol, 1.0 eq) and sodium triacetoxyborohydride (1.32 g, 6.29 mmol,3.2 eq) were suspended in 17 mL 1,2-dichloroethane. Then, triethylamine (0.55mL, 3.93 mmol, 2.0 eq) was added and the reaction mixture was stirred at rtovernight. Then, water was added and the resulting phases were separated bythe use of a Whatman filter. The volatile components of the organic phase wereremoved in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/ethyl acetate 9/1 -> hexane/ethyl acetate 1/1) to give 320mg (63% yield of theory) of the title compound.UPLC-MS (Method 1): R = 0.56 mm; MS (EI0): m/z = 248 [M+H].

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

Reference of 330786-09-9,Some common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, molecular formula is C6H4Cl2N2O2, 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 1 Methyl 3,5-dichloropyrazine-2-carboxylate Jl (lOg, 48.3 mmol) was treated with sodium methoxide in MeOH (97 ml, 48.3 mmol) at RT for 3 hour. It was filtered and the filtrate was concentrated under reduced pressure. The residue was washed with water and dried to give compound J2 (9.79 g). LCMS for J2: m/e = 203 (M+l).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Wen-Lian; HE, Shuwen; WALSH, Shawn, P.; CUMMING, Jared, N.; (70 pag.)WO2016/118404; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

98-97-5, name is Pyrazine-2-carboxylic acid, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C5H4N2O2

General procedure: The N-hydroxysuccinimideesters of pyrazinecarboxylic acid and (5)-(+)-ibuprofen were prepared by dissolving the starting acid (0.200 g, 1.0 equiv) in dry tetrahydrofuran. With stirring at 0 C, NHydroxysuccinimide (1.0 equiv) was added followed by N,N-dicyclohexylcarbodiimideequiv). The mixture was warmed to ambient temperature and stirred for 24 h. The N,Ndicyclohexylurea was removed by filtration and the filtrate was concentrated to afford a solid that was purified by column chromatography.[001481 2, 5-Dioxopyrrolidin-1-yl pyrazine-2-carboxylate 14. The cmde white solid was purified by column chromatography (Si02, acetone/dichloromethane, 1:4) to give a white solid (0.2757 g, 77%). Mp: 161 – 164 C. ?H NMR (300 MHz, CDC13): oe 9.40 (d, J= 1.41H), 8.90 (d, J= 2.3 Hz, 1H), 8.83 (dd, J= 2.4, 1.5 Hz, 1H), 2.95 (s, 4H). ?3C NMRMHz, CDC13): oe 168.9, 159.6, 149.3, 147.1, 145.2, 140.2, 25.8. JR (neat): 3501, 3324, 3276, 3078, 2929, 2851, 1875, 1806, 1785, 1703, 1653, 1626, 1571, 1533, 1468, 1449, 1420, 1399, 1360, 1306, 1260, 1243, 1203, 1183, 1153, 1075, 1060, 1048, 1025, 1011, 995,892, 876, 853, 811, 782, 764, 713 cmi. HRMS calcd. for C9H8N304 [M+Hj 222.0509, found 222.0502.

The synthetic route of 98-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY; PIRRUNG, Michael, C.; BAKAS, Nicole, A.; BACHMANN, Andre; (89 pag.)WO2017/156471; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem