Tag: M.W=200-300

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. 1422772-78-8, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1422772-78-8

Step 5. Methyl 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylate. To a 0 C. suspension of 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (145 g, 602 mmol) in MeOH (1.5 L) was added dropwise SOCl2 (93 g, 781 mmol) over a period of 40 min. after the addition, the resulting mixture was heated to reflux for 4 hours, which time suspended solution became clear and then yellow solid was precipitated. TLC (petroleum ether/EtOAc, 1:1) showed starting material was consumed completely. The reaction mixture was evaporated to dryness, which was triturated with MTBE to give methyl 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylate (109 g, 71%) as a yellow solid.

According to the analysis of related databases, 1422772-78-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Thorarensen, Atli; Brown, Matthew Frank; Casimiro-Garcia, Agustin; Che, Ye; Coe, Jotham Wadsworth; Flanagan, Mark Edward; Gilbert, Adam Matthew; Hayward, Matthew Merrill; Langille, Jonathan David; Montgomery, Justin Ian; Telliez, Jean-Baptiste; Unwalla, Rayomand Jal; US2015/158864; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1379338-74-5, 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. 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

A solution of tert-butyl 3-(aminomethyl)-5-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate (4.74 g, 13.7 mmol), 5,7-dichloropyrido[4,3-b]pyrazine (2.75 g, 13.7 mmol) and DIPEA (2.12 g, 16.4 mmol) in THF (20 mL) was stirred at room temperature for 48 hours. The volatiles were removed under reduced pressure and the residue was treated with ethyl acetate, washed with brine, dried over Na2SO4, filtered, and concentrated to give the title compound.

The chemical industry reduces the impact on the environment during synthesis 5,7-Dichloropyrido[3,4-b]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; Su, Wei-Guo; Deng, Wei; Ji, Jianguo; US2014/121200; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6966-01-4,Some common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, 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 methyl 3-amino-6-bromopyrazine-2-carboxylate (100 mg, 0.43 mmol) in MeOH (5 mL) was added 2 mL of NaOH aqueous solution (5 N). After being stirred at 50C for 4 h, the mixture was cooled and acidified with 1 M HCl to a pH of 2. The precipitate was collected by filtration and washed with water to afford the product of 3-amino-6- bromopyrazine-2-carboxylic acid (90 mg, yield: 96%). XH-NMR (DMSO-ifc, 400 MHz) delta 8.38 (s, 1H), 7.51-7.56 (m, 2H). MS (M+H)+: 218 / 220.

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-6-bromopyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 110223-15-9, name is 2-Amino-3-benzyloxypyrazine, 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 110223-15-9, Computed Properties of C11H11N3O

General procedure: For aromatic urea derivatives; the appropriate aromatic isocyanate(3.0 mmol) was added to a solution of the appropriate 2-amino-3-benzyloxy pyrazine derivative (2.5 mmol) in THF(10 mL). The reaction was refluxed for 3e6 h. After cooling, thereaction mixture was evaporated and the residue was purified byprecipitation in cold methanol and filtered to give the targetcompound(s). For aliphatic urea derivatives; the appropriatealiphatic isocyanate derivative (1.02 mmol) was added to a solutionof the appropriate 2-amino-3-benzyloxy pyrazine derivative(0.85 mmol) in dry THF (5 mL) in the presence of NaH (60% inmineral oil, 68 mg, 1.71 mmol). The reaction was refluxed for 5 h.After cooling, the reaction mixture was evaporated and the residuewas purified by flash column chromatography (SiO2, EA/n-Hex 1/4).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-3-benzyloxypyrazine, and friends who are interested can also refer to it.

Reference:
Article; Elkamhawy, Ahmed; Park, Jung-eun; Hassan, Ahmed H.E.; Pae, Ae Nim; Lee, Jiyoun; Paik, Sora; Park, Beoung-Geon; Roh, Eun Joo; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 268 – 278;,
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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H3Br2N3

A solution of intermediate 1-01(15 g, 59.3 mmol) inmorpholine (15 ml, 178 mmol) was heated at 120 C. in a Parr reactor for 48 h. A brown solid appears. The solid was suspended in DCM and washed with NaHCO3 aq. sat (twice). The organic phase was dried (NaSO4), filtered and evaporated to dryness to obtain 1-02, 14.8 g of a brown solid(Y: 96%)

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); Serrano Marugan, Manuel; Pastor Fernandez, Joaquin; Martinez Gonzalez, Sonia; Ortega Molina, Ana; Bischoff, James R.; Oyarzabal Santamarina, Julen; (220 pag.)US9993554; (2018); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 63744-22-9, 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. 63744-22-9 name is 6,8-Dibromoimidazo[1,2-a]pyrazine, 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.

A mixture of 3,4-dimethoxyaniline (18.0 g, 118 mmol), 6,8- dibromoimidazo[1 ,2-a]pyrazine (25.0 g, 90.4 mmol), and Lambda/,Lambda/-diisopropylethylamine (11.7 g, 90.4 mmol) in DMF (500 ml_) was stirred at 120 0C overnight. After this time, the reaction was cooled to room temperature and concentrated to approximately 100 ml_ under reduced pressure. The dark brown reaction mixture was poured into ice-cold water (300 ml_) and stirred for 10 min. The resulting brown precipitate was filtered and the filter cake washed with water (100 ml_). The filter cake was dried under vacuum and recrystallization from methanol (-800 ml_) to afford 6-bromo-Lambda/-(3,4,5- trimethoxyphenyl)imidazo[1 ,2-a]pyrazin-8-amine (2) (23.3 g, 74%) as a light brown needle-shaped solid: 1H NMR (300 MHz, DMSO-Gf6) 9.81 (s, 1 H), 8.22 (s, 1 H), 7.93 (s, 1 H), 7.75 (d, J = 2.4 Hz, 1 H), 7.62 (s, 1 H), 7.53 (dd, J= 8.7, 2.4, 1 H), 6.94 (d, J= 8.7 Hz, 1 H), 3.77 (s, 3H), 3.75 (s, 3H); ESI MS m/z 349.2 [M + H]+; HPLC, 6.92 min, >99% (AUC).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6,8-Dibromoimidazo[1,2-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; CGI PHARMACEUTICALS, INC.; MITCHELL, Scott A.; CURRIE, Kevin S.; BLOMGREN, Peter A.; KROPF, Jeffrey E.; LEE, Seung H.; XU, Jianjun; STAFFORD, Douglas G.; HARDING, James P.; BARBOSA, Jr., Antonio J.; ZHAO, Zhongdong; WO2010/68257; (2010); 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

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.

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).

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; 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

Related Products of 1458-01-1,Some common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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.

(1) A mixture of 20 g (99.0 mmol) of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (see U.S. Pat. No. 4,029,816 for an example of how to obtain this material) and 17 g (230.0 mmol) of N-methylethylenediamine was heated at reflux under an inert atmosphere for 30 hours. The rection mixture was cooled to ambient temperature and the solid was dissolved in 100 ml of tetrahydrofuran. The solution was filtered and evaporated. The residue was crystallized from 2-propanol. There was obtained 15.0 g (61.2 mmol, 61percent) of 3,5-diamino-6-chloro-N-(2-methylaminoethyl)pyrazine-2-carboxamide; mp 142.5°-143° C. Analysis calculated for; C8 H13 ClN6 O: C, 39.27; H, 5.35; N, 34.35; Found: C, 39.28; H, 5.26; N, 34.55.

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-diamino-6-chloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; ICI Americas Inc.; US4910202; (1990); A;,
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. 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 330786-09-9

Methyl 3,5-dichloropyrazine-2-carboxylate (5.0 g, 24.2 mmol) was dissolved in a 9: 1 mixture of dry tetrahydrofuran (242 mL) and methanol (27 mL). The mixture was cooled to 1.5-2 C with an ice/water bath and stirred at this temperature for 10 min. A 2 M solution of lithium borohydride in THF (13.3 mL, 26.6 mmol) was then added carefully keeping the temperature below 4-5 C. After addition, the reaction mixture was stirred for an additional 10-15 min at 0-4 C. Methanol (120 mL) was added to the flask and the mixture stirred for 15 min at rt. The reaction was slowly poured into a mixture of 1 M HC1 solution (100 mL) and ethyl acetate (200 mL). The resulting mixture was stirred at rt for 15 min. The aqueous layer was extracted with ethyl acetate (3 x 150 mL) and the combined organics washed with brine (2 x 100 mL), dried over anhydrous MgS04, filtered, and concentrated under reduced pressure. (3,5-Dichloropyrazin-2-yl)methanol (4.3 g, 99% yield) was obtained as a yellow oil after drying under high vacuum for 2 h. 1H-NMR (500 MHz, CDCI3) d 8.52 (s, 1H), 4.85 (s, 2H).

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; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem