Tag: M.W=100-200

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. 912773-21-8, name is 2-Bromo-5-chloropyrazine, A new synthetic method of this compound is introduced below., Safety of 2-Bromo-5-chloropyrazine

A mixture of 2-bromo-5-chloro-pyrazine (2 g, 10.34 mmol), 3-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-[(lR)-2,2,2-trifluoro-l- methyl-ethoxy]pyridine (3.12 g, 9.31 mmol), Pd(dppf)Cl2 (1.13 g, 1.55 mmol) and CS2CO3 (6.74 g, 20.68 mmol) in l,4-dioxane (100 mL) and water (10 mL) was stirred under N2 at 50 C for 5 hours. After cooling to room temperature, the mixture was diluted with EtOAc (10 mL), filtered with silica gel, eluted with EtOAc (20 mL) and concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 20%) to give the product (2500 mg, 7.21 mmol, 70% yield) as a solid. ‘H NMR (400MHz, CDCI3) dH= 8.77 (d, 1H), 8.64 (d, 1H), 8.53 (d, 1H), 8.08 (dd, 1H), 6.00 – 5.83 (m, 1H), 1.59 (d, 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; PRAXIS PRECISION MEDICINES, INC.; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; MARTINEZ BOTELLA, Gabriel; REDDY, Kiran; WITTMANN, Marion; (0 pag.)WO2019/232209; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 54608-52-5, 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 54608-52-5 as follows.

Step 1 2,2-difluoro-N’-pyrazin-2-yl-acetohydrazide difluoroacetate Pyrazin-2-yl-hydrazine 23a (1 g, 9 mmol) was added in an eggplant-shaped bottle (25 mL), followed by dropwise addition of difluoroacetic anhydride (4 g, 22.98 mmol) at 0 C. After stirring at room temperature for 3 hours, the reaction mixture was concentrated under reduced pressure to obtain crude 2,2-difluoro-N’-pyrazin-2-yl-acetohydrazide difluoroacetate 23b (2 g) as a brown oil. The product was used directly in the next reaction without purification.

According to the analysis of related databases, 54608-52-5, 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

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. 14667-55-1, name is 2,3,5-Trimethylpyrazine, A new synthetic method of this compound is introduced below., SDS of cas: 14667-55-1

Take 2,3,5-trimethylpyrazine (16.3 mL, 98.7 mmol) in a 500 mL round bottom flask, glacial acetic acid (60 mL) and 30% hydrogen peroxide (50 mL) were slowly added with a constant pressure funnel while stirring in an ice bath, the reaction solution was stirred and heated in an oil bath at 60 C, an equal amount of 30% hydrogen peroxide was added dropwise to the reaction solution, and the mixture was stirred for 20 hours, cooled to room temperature, water (50 mL) was added, rhoEta was adjusted = 9 with saturated K2C03, extracted with DCM (200mLX4), the organic phase was washed with saturated brine (200 mL), dried over anhydrous sodium sulfate, the organic phase was concentrated to give 12.4 g of a pale yellow oily liquid, yield was 76%.

The synthetic route of 14667-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guizhou Medical University; Fan Lingling; Tang Lei; Li Yi; Li Yong; Liu Jian; Chu Liangzhao; (28 pag.)CN108558833; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4858-85-9,Some common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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. Preparation of the intermediate compounds; A1. Preparation of intermediate compound 1; 2,3-Dichloropyrazine (10 g, 62.12 mmol) and 1-(phenylmethyl)-4-piperidinamine (13.73 mL, 67.12 mmol) were dissolved in DMF (60 ml). Then Na2CO3 (10.09 g, 1 14.10 mmol) was added. The reaction was stirred at 130 0C for 16 hours. The solid was filtered off, washed with AcOEt and the solvent was evaporated till dryness. The product was dissolved in AcOEt, washed with H2O and brine, dried with MgSO4 and evaporated under vacuum yielding 15 g of the desired intermediate compound 1 (74 %).The product was used without any further purification.

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

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/122173; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 889447-19-2,Some common heterocyclic compound, 889447-19-2, name is 2-Chloro-5H-pyrrolo[2,3-b]pyrazine, molecular formula is C6H4ClN3, 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 1M solution of iodine chloride in dichloromethane (4ml, 4mmol) was added dropwise to an ice-cold solution of 2-chloro-5H-pyrrolo[2,3-&]pyrazine (4) in N-methylpyrrolidone (residual from previous step) and pyridine (5ml). The reaction mixture was stirred for 60 minutes at O0C and then was concentrated in vacuo. The residue was purified by flash chromatography, using as eluent pentane/EtOAc 0% to 50%, to give the title compound (820 mg, 75% over two steps). 1Eta NMR (DMSO-d6) 8.2 (lEta,s), 8.4 (IH, s). MS(ES+): 280

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-5H-pyrrolo[2,3-b]pyrazine, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2006/58074; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 69214-33-1, 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. 69214-33-1, name is 8-Chloroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

To the solution of compound 9 (6.47 g, 42.13 mmol) indichloromethane (140 ml) N-bromosuccinimide (7.50 g,42.13 mmol) was added and the mixture was stirred at roomtemperature for 3 h. The reaction mixture was diluted withdichloromethane and stirred with 10% aqueous sodium carbonatesolution for 1 h before the layers were separated. The organic layerwas washed with water (2), dried over sodium sulphate, filteredand concentrated under reduced pressure. The crude product was triturated with diisopropyl ether and filtered to give the titlecompound (14.40 g)

The chemical industry reduces the impact on the environment during synthesis 8-Chloroimidazo[1,2-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Garamvoelgyi, Rita; Dobos, Judit; Sipos, Anna; Boros, Sandor; Illyes, Eszter; Baska, Ferenc; Kekesi, Laszlo; Szabadkai, Istvan; Szantai-Kis, Csaba; Keri, Gyoergy; Oerfi, Laszlo; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 623 – 643;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 312736-49-5, name is 3,5-Dichloropyrazine-2-carboxylic acid, 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 312736-49-5, category: Pyrazines

To a 100 mL round-bottomed flask, 3,5-dichloropyrazine-2-carboxylic acid(3.65 g, 18.9 mmol) and NaHCO3 (4.70 g, 22.7 mmol) are dissolved in dimethylformamide (38mL). lodomethane (7.14 mL, 113 mmol) is added dropwise and the resulting mixture is stirred overnight at room temperature. The mixture is diluted in water (50 mL) and extracted with ethyl acetate (3 x 15 mL). The combined organic layers are washed with brine (4 x 10 mL), dried over anhydrous Na2504, filtered and concentrated under reduced pressure. Methyl 3,5-dichloropyrazine-2-carboxylate (3.77 g, 96%) is obtained as a yellowish solid after drying under high vacuum for 2-3 h. NMR ?H (500 MHz, CDC13) oe 8.57 (s, 1H), 4.03 (s, 3H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; GIORDANETTO, Fabrizio; GREISMAN, Jack, Benjamin; MARAGAKIS, Paul; TAYLOR, Alexander, M.; DIPIETRO, Lucian, V.; KELLEY, Elizabeth, H.; LESCARBEAU, Andre; MURCKO, Mark, Andrew; PIERCE, Levi Charles, Thomas; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; BHAT, Sathesh; THERRIEN, Eric; DAHLGREN, Markus, Kristofer; (156 pag.)WO2018/81091; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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: (3-Chloropyrazin-2-yl)methanamine hydrochloride

To a solution of(3S,6S)-l-((benzyloxy)carbonyl)-6-(hydroxymethyl)piperidine- 3-carboxylic acid (0.78 g, 2.66 mmol) in 20 mL of DMF was added HATU (1.21 g, 3.2 mmol). After stiring for 30 min under N2, (3-Chloro-pyrazin-2-yl) methanamine hydrochloride (0.48 g, 2.66 mol) and Et3N (0.8 g, 7.98 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours under N2. The mixture was partitioned between EA and water. The organic layer was washed with 1 N HC1 and water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford (2S,5R)-benzyl 5-(((3- chloropyrazin-2-yl)methyl)carbamoyl)-2-(hydroxymethyl)piperidine-l -carboxylate (0.7 g, 63.0% yield). 1HNMR (400 MHz, CD3OD): delta= 8.50 ~ 8.54 (m, 1 H), 8.35 (d, / = 2.4 Hz, 1 H), 7.31 ~ 7.41 (m, 5 H), 5.16 (s, 2 H), 4.63 (s, 2 H), 4.34 ~ 4.38 (m, 1 H), 4.21 ~ 4.25 (m, 1 H), 3.72 ~ 3.77 (m, 1 H), 3.63 ~ 3.67 (m, 1 H), 3.01 ~ 3.07 (m, 1 H), 2.46 ~ 2.54 (m, 1 H), 1.80 ~ 1.93 (m, 3 H), 1.61 ~ 1.71 (m, 1 H). MS (ESI): M/Z (M+l): 419.1

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.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 5-chloropyrazine-2-carboxylate

Dissolve 5-chloro-pyrazine-2-carboxylic acid methyl ester (10.0 g, 57.9 mmol) in THF (65 mL) and MeOH (65 mL). Cool the solution to 0 0C before adding IN NaOH (63.7 mL) with stirring. Warm the mixture to room temperature and stir for 5 h. Concentrate the mixture in vacuo to 1/3 volume. Quench with IN HCl (75 mL) to form a white precipitate. Dilute with CH2Cl2 (200 mL) and filter. Wash the filter cake with water and CH2Cl2. Separate the phases, dry the organic phase over MgSO4, filter, and concentrate. Add the aqueous layer to the concentrated organic residue and concentrate. Purify by silica gel flash column chromatography, eluting with 40% ethyl acetate/n-hexane, followed by 10% MeOH, 3% acetic acid and 87% EPO CH2Ch- Collect the mixed fractions and concentrate. Take up the resulting solid with CH2CI2 (50 mL) and H2O (50 mL) and stir. Filter the solid and add it to the first filter cake. Add 5.0N NaOH to the filtrate to make the solution basic. Separate the two layers. Discard the organic layer, add 5.0N HCl to the aqueous layer until acidic. Extract with CH2Cl2 (3 x 100 mL). Dry the organic layer over Na2SO4, filter, and concentrate. Add the solid to the pure fractions from the column. Combine the pure filter cakes with the pure fractions from the column, yielding the desired product (8.46 g, 92%). mass spectrum (exact mass): 157.99.

According to the analysis of related databases, 33332-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/66173; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 22047-25-2, name is Acetylpyrazine, 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 22047-25-2, Formula: C6H6N2O

In a 250mL round-bottom flask, 2-acetylpyrazine (1.22g, 10.00mmol) was added to a solution of 4-chlorobenzaldehyde (0.700g, 5.00mmol) in EtOH (30mL) upon stirring. KOH pellets (0.560g, 10.0mmol) were then added, and followed by aqueous NH3 (28%, 25mL). The resulting brownish solution was stirred at room temperature overnight, during which time gray solid had formed. The solid was collected by filtration, washed with EtOH and dried in vacuo over P2O5. L2 was isolated as pure product (1.00g, 58.0%). UV-Vis lambdamax/nm (2.5×10-5moldm-3, CH2Cl2-MeOH) 250 (epsilon/103dm3mol-1cm-1 18.7), 285 (26.1), 320sh (8.1). FT-IR (solid, cm-1): 1603s, 1571w, 1521w, 1496s, 1472m, 1428m, 1372s, 1245w, 1117m, 1050m, 1017s, 852m, 822s, 738w, 690m. 1H NMR (400MHz, CDCl3)delta 9.92 (s, 2 H, HA3), 8.85(dd, J=6.4, 1.0Hz, 4 H, HA5/A6), 8.72 (s, 2 H, HB3), 8.03(d, J=8.7Hz, 2H, HC3), 7.67 (d, J=7.67Hz, 2 H, HC2) ppm; 13CNMR (101MHz, CDCl3)delta154.39, 149.58, 148.79, 145.59, 144.10, 143.11, 134.71, 129.44, 128.95, 118.97ppm. HR-MS: m/z 346.0863 [M+H]+ (calc. 346.0859), 368.0679 [M+Na]+ (calc. 368.0679).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Acetylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Li; Liu; Xiong, Hangxing; Chan, Corinna; Manke, David R.; Golen, James A.; Zhang, Guoqi; Polyhedron; vol. 132; (2017); p. 64 – 69;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem