Month: July 2021

Electric Literature of 77112-53-9,Some common heterocyclic compound, 77112-53-9, name is Imidazo[1,2-a]pyrazine-2-carboxylic acid, molecular formula is C7H5N3O2, 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: Imidazo[1,2-a]pyrazine-2-carboxylic acid (5) (1.0 equiv.) Mukaiyama?s reagent and 2-chloro-1-methylpyridinium iodide (1.2 equiv.) were suspended in DMF (5.0 mL) under nitrogen atmosphere. Into the reaction mixture, aliphatic/aromatic amines (6a-l) (1.0 equiv.) and 1-methylimidazole (2.0 equiv.) were added. A homogeneous solution was formed after a gentle stirring. The reaction mixture was sealed in a microwave glass reactor and then irradiated by microwave oven at a constant temperature of 80 C with continuous stirring (1 min ramp, 15 min reaction time). After the reaction was completed, the solvent was removed through a rotary evaporator and the resulting residue was extracted by a biphasic system of 45 mL diethyl ether and 45 mL water. After the layer separation, the ether layer was dried by anhydrous sodium sulphate, followed by an evaporation of ether to get compounds 7a-l (Scheme-I).

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

Reference:
Article; Jyothi, Boggavarapu; Madhavi, Nannapaneni; Asian Journal of Chemistry; vol. 32; 1; (2020); p. 84 – 90;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 56423-63-3, 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. 56423-63-3, name is 2-Bromopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Reaction Scheme 6EXAMPLE 30: l-(4-methoxybeDzylV3-methyl-5-(pyrazin-2-ylVlH-pyrazolor3.4- blpyridine To a stirred solution of compound 8 (230 mg, 0.627 mmol) and 2-bromopyrazine 43 (100 mg, 0.63 mmol) in DME (3 mL), ethanol (1 mL) and water (0.2 mL) was added sodium carbonate (135 mg, 1.26 mmol) and was degassed for 10 min followed by the charging Pd(PPh3)4 (7.5 mg, 0.03 equivalent). The resulting reaction mixture was purged with N2 and degassing was submitted for heating at 80C overnight under pressure in a sealed tube. After completion of the reaction the reaction was diluted with ethyl acetate and water. The organic layer was separated and aqueous phase was extracted with ethyl acetate. The combined organic layer was washed with brine and dried over sodium sulphate and evaporated. The crude product was flash chromatographed with 100-200 mesh silica gel eluting the pure compound at 20% ethyl acetate in hexane as off white colored solid of compound 44 in 30 mg. The product 44 was confirmed by 1H NMR (400 MHz, CDC13) delta: 9.18 (s, 1H), 9.17 (s, 1H), 9.10 (d, J=1.58 Hz, 2H), 8.67 (s, 1H), 8.64 (s, 1H), 7.35 (d, 2H), 6.84 (d, 1H), 5.62 (d, 2H), 3.76 (s, 3H), 2.62 (s, 3H).

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

Reference:
Patent; ARRIEN PHARMAEUTICALS LLC; VANKAYALAPATI, Hariprasad; APPALANENI, Rajendra, P.; REDDY, Y., Venkata Krishna; WO2012/135631; (2012); 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. 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H12N2O

The obtained 7.5 g of TMP-OH (49.3 mmol) was dissolved in 50 ml of absolute ethanol to add active manganese dioxide.(6.4g, 73.6mmol) was oxidized and reacted in an oil bath at 84 C for 2 h. After the TLC reaction was completed,The reaction solution was carefully filtered with a five-layer filter paper while hot, and the manganese dioxide powder was removed.After filtration, a clear filtrate was obtained, which was evaporated to dryness under reduced pressure on a rotary evaporator. Wet loading column chromatography:The mobile phase EA:PE (1:5) was separated and purified, and the fraction was monitored by TLC. Collecting the compound 1a-4 fraction,Combine the same fraction and distill it to obtain a crystalline white solid.5.5g (36.7mmol),[M+H]+=151 is 1a-4 (TMP-CHO), yield 75%.

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 75907-74-3.

Reference:
Patent; Guangzhou Xique Pharmaceutical Co., Ltd.; Wang Yuqiang; Yao Hui; Wu Chuanbin; Tao Liang; Sun Yewei; (27 pag.)CN103804309; (2019); B;,
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, COA of Formula: C6H6N2O

[0146] To a stirred solution of compound I (2 g; 16.4 mmol; 1 eq) in methanol (20 mL) were added ammonium acetate (12.6 g; 164 mmol; 10 eq) and sodium cyanoborohydride (1 g; 16.4 mmol; 1 eq) and the resulting mixture was stirred at 23 C for 17 h. The mixture was quenched with water (50 mL) and the organic components were extracted with ethyl acetate (2 x 200 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and the solvents were removed in vacuo to afford crude compound, which was purified by silica gel (230-400 mesh) column chromatography, eluting with 10% MeOH/CH2C12, to afford the title compound (0.8 g, 40%). 1H NMR (CDC13) oe 8.60 (s, 1H), 8.49 (m, 1H), 8.43 (d, 1H, J= 2Hz), 4.20 (m, 1H), 1.45 (d, 3H, J= 7Hz).

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; ASANA BIOSCIENCES, LLC; THOMPSON, Scott; VENKATESAN, Aranapakam; PRIESTLEY, Tony; KUNDU, Mrinal; SAHA, Ashis; WO2015/95128; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 36070-80-1, name is 5-Chloropyrazine-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 36070-80-1, Application In Synthesis of 5-Chloropyrazine-2-carboxylic acid

To a cooled solution of 26 (3 g, 18.92 mmol, 1.0 eq), in N,N-dimethylformamide (30 mE) was added 1-[l3is (dimethylamino)methylene] -1 H-i ,2,3-triazolo[4,5-b]pyri- dinium 3-oxid hexafluorophosphate (8.65 g, 22.70 mmol, 1 .2 eq) and stirred at room temperature for 20 mm. Reaction mixture again cooled diisopropylethylamine (7.32 mE, 56.76 mmol, 3.0 eq) was added followed by addition of dimethylamine (0.851 g, 18.92 mmol, 1.0 eq). The reaction mixture was stirred at room temperature for 2 h. After completion of reaction, reaction mixture was transferred into water and product was extracted with ethyl acetate. Organic layer was combined, washed with brine solution, dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was thrther purified by column chromatography and the compound was eluted in 0.9% methanol in dichioromethane to obtain 26.1(2.5 g, 71.18%). MS(ES): mlz 186.61 [M+H].

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; Nimbus Lakshmi, Inc.; Masse, Craig E.; Greenwood, Jeremy Robert; Mondal, Sayan; Cowen, Scott D.; McLean, Thomas H.; (624 pag.)US2019/31664; (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 38557-72-1 as follows. Quality Control of 2-Chloro-3,5-dimethylpyrazine

Step 4: Synthesis of 3,5-Dimethyl-2-(6-phenylnaphthalen-2-yl)pyrazine (abbreviation: Hdm6p2npr)First, into a recovery flask equipped with a reflux pipe were placed 0.24 g of 2-chloro-3,5-dimethylpyrazine, 0.41 g of 6-phenylnaphthalene-2-boronic acid, 0.18 g of sodium carbonate, 0.008 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2), 10 mL of water, and 10 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was irradiated with microwaves (2.45 GHz, 100 W) for 30 minutes, so that heating was performed. Then, the reaction container was cooled to 50 C. or less. Water was added to the reaction solution, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled, whereby Hdm6p2npr, which is the pyrazine derivative to be produced, was obtained (as a white powder in 82% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 4 is illustrated in the following (d-4).

According to the analysis of related databases, 38557-72-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US2011/245495; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, 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. Quality Control of 2-Chloropyrazine

Under nitrogen protection,To a solution of 2,2,6,6-tetramethylpiperidine (72.8 g, 516.3 mmol)In 500 mL of dry THF solution,N-BuLi (346 mL, 553.7 mmol, 1.6 mol / L THF) was slowly added dropwise at -78 &After completion of the reaction, the reaction mixture was warmed to 0 C and the reaction was continued for 20 min.The reaction mixture was then cooled to -78 C,A solution of 2-chloropyrazine (50 g, 436.3 mmol) in THF (100 mL) was added dropwise to the reaction mixture,30min plus finished,The color of the reaction mixture changed from light yellow to dark brown,The reaction was continued for 10 min at -78-0 degC.DMF (84 ml, 1092 mmol)Was dissolved in THF (50 mL) dropwise dropwise into the reaction mixture,Control the reaction system temperature at -70 ~ -78 ,10min plus finished,The reaction was stirred at -78 C for 2 h.To the reaction mixture was then added MeOH (800 mL)To the reaction mixture, NaBH4 (33 g, 868 mmol) was added portionwise,After the addition, the reaction mixture was allowed to rise to room temperature and stirring continued for 2 h,TLC shows the raw material reaction is complete,The reaction solution was quenched with saturated NH4Cl,DCM (1 L x 3) was extracted three times,The organic phase was washed with water,Anhydrous Na2SO4 fully dried,After vacuum evaporation, the residue was purified by silica gel column (PE / EA = 100/1 to 5/1) to give 60 g of the title compound

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

Reference:
Patent; Chengdu Beite Pharmaceutical Co., Ltd.; Chengdu Hai Borui Pharmaceutical Co., Ltd.; Li Yingfu; Huang Haoxi; Liu Guanfeng; Chen Tonghun; Ren Junfeng; Su Zhonghai; (96 pag.)CN106831787; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 153800-11-4, These common heterocyclic compound, 153800-11-4, name is 2-Ethynylpyrazine, 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 231(100mg, 0.282mmo1) and 10(58.8mg, 0.565mmo1) in 2OmL of Et3N was added Pd(PPh3)2C12 (991mg, 0Oi4mmol) and Cul (538mg, 0O28mmol). The mixture was protected with N2 atmosphere, then was heated at 70C for 4 hours. TLC analysis showedcomplete conversion of starting material to a major product. The reaction mixture was then concentrated in vacua The crude product was purified by Prep-HPLC to give the target product Compound 125(23mg, yield: 24.66%).LCMS: in/z 331 (M+HY?H NMR (400 MHz, CDCI3): d 8.83 (d, J:::: 6.4 Hz, 11:1), 862 (s, 11:1), 854 (s, 1H), 793 (d, J:::2.4 Hz, IH), 7.79-7.75 (m, 2H), 735-733 (m, 2H), 6.79 (d, J= 2.4 Hz, 1H).

The synthetic route of 153800-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6705-33-5, name is Pyrazin-2-ylmethanol, 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 6705-33-5, Safety of Pyrazin-2-ylmethanol

Pyrazin-2-ylmethanol (1.5 g) was dissolved in DMA (25 ml) and the solution was cooled to 0C. 60% Sodium hydride dispersion in oil (0.6 g) was added portionwise and the mixture was stirred for 10 minutes at 0C. A solution of 3-chloro-4-fluoronitrobenzene (2.18 g) in DMA (25 ML) was added over 15 minutes and the reaction mixture was allowed to warm to room temperature and stirred for 3 hours. Saturated ammonium chloride (100 ml) was added, and the precipitated solid was filtered off and purified by chromatography eluting with 50% ethyl acetate/iso-hexane. The appropriate fractions were concentrated to give 3-chloro- 4- (2-PYRAZINYLMETHOXY) nitrobenzene as a brown solid (1.25 g, 38%).

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, Pyrazin-2-ylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/26151; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 122-05-4, name is Pyrazine-2,5-dicarboxylic 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 122-05-4, Safety of Pyrazine-2,5-dicarboxylic acid

For complex 2, a mixture of Co(NO3)26H2O (30mg,0.1mmol), bimb (20 mg, 0.05mmol) and H2pdc (17mg,0.1mmol) was dissolved in 5mL of DMF, and the mixture wasstirred for 30 min in the air. After the addition of 2mL of water,the mixture was transferred and sealed in a 25mL Teflon-linedreactor and heated to 120 C for 72 h, and thereafter cooled toroom temperature at a rate of 5 C/h. Pink block crystals of 2were obtained in 54% based on Co(NO3)26H2O), water byDMF and dried in the air. Anal. Calcd for 2 (C33H25CoN9O5):C, 57.73; H, 3.67; N, 18.36%; Found: C: 57.23; H: 3.61; N:18.92%. IR (KBr, cm1): 3385(m), 2360(w), 1944(w), 1829(w),1610(m), 1583(m), 1534(m), 1446(m), 1398(w), 1315(w),1186(w), 1142(w), 1109(w), 1051(w), 1014(w), 922(w), 905(w),862(w), 810(w), 779(m), 746(w), 709(w), 670(w), 635(w),592(w), 526(w), 477(w), 426(w).

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:
Article; Xu, Su-Peng; Qin, Feng-Ting; Zheng, An-Xiong; Li, Jiang-Tao; Inorganic and Nano-Metal Chemistry; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem