Month: September 2021

Adding a certain compound to certain chemical reactions, such as: 14508-49-7, name is 2-Chloropyrazine, 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 14508-49-7, COA of Formula: C4H3ClN2

Intermediate 65; 4-Pyrazin-2-yl-lH-indole; 4-Bromoindole (0.1 g, 0.51 mmol), bis(pinacolato)diboron (0.172 g, 0.77 mmol), potassium acetate (0.075 g, 0.765 mmol) and PdCl2 (0.022 g, 0.031 mmol) were dissolved in DME (3 mL) and heated in the microwave for 900 seconds at 125C. The reaction was cooled and NaHCO3 (0.129 g, 1.53 mmol), 2-chloropyrazine (0.087 g, 0.77 mmol) tetrakis(triphenylphosphine)palladium (0.0295 g, 0.026 mmol), H2O (1 mL) and DME (1 mL) were added and the mixture was stirred in the microwave for 900 seconds at 120C. The mixture was diluted with dichloromethane and filtered. The filtrate was washed with water (2x), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography using 2.5% to 5% CH3OH in dichloromethane. Not pure, purified by flash chromatography using hexane/EtOAc 7:3 to 1:1 as the eluent. Yield: 93 mg (47%). White solid. MS (electronspray; [M+H]+) m/z 196.3.

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; BIOVITRUM AB (publ); WO2008/3703; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 939412-86-9, A common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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 mixture of compound V (49.8 g), DCM (500 mL) and DMF (5 mL) in a 500 mL three-neck flask, oxalyl chloride (38 g, 1.5 eq) was added at 0~10 C. The reaction mixture was warmed to RT. After completion of the reaction, the solvent was removed by concentration. DCM (200 mL) was added to obtain the compound VI solution in DCM. (0099) To a mixture of compound VII (30 g), DCM (240 mL) and TEA (6 eq) in a 1000 mL three-neck flask at 0~10 C, the solution of compound VI in DCM obtained from the above step was added dropwise, the reaction mixture was warmed to RT. After the reaction was completed, water (300 mL) was added to quench the reaction. The organic phase was washed with IN HCI aqueous solution (500 mL), saturated NaHC03 aqueous solution (500 mL) and water (500 mL). The organic phase was concentrated under vacuum. The crude product was recrystallized from IPAc/Heptane to afford compound VIII (61 g, 98% yield, 99.7% chiral purity).

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; WANG, Peng; LI, Pixu; GU, Xiangyong; GE, Yadong; WANG, Zhong; GAO, Feng; DU, Qiangqiang; (25 pag.)WO2019/90269; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 118853-60-4, 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 118853-60-4 as follows.

Into a 50-mL round-bottom flask was placed pyridine (25 mL), methyl 6- aminopyrazine-2-carboxylate (1 g, 6.53 mmol, 1.00 equiv) and 1-methyl-1H-pyrazole-4- carbonyl chloride (1.13 g, 7.82 mmol, 1.20 equiv). The resulting solution was stirred for 2 h at 25 oC in an oil bath. The resulting mixture was concentrated under vacuum at 55 oC for 1 h. This resulted in 1.72 g (93% purity) of methyl 6-(1-methyl-1H-pyrazole-4-amido)pyrazine-2- carboxylate as a yellow solid.

According to the analysis of related databases, 118853-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; PADILLA, Fernando; TOOGOOD, Peter, L.; CHEN, Shoujun; (331 pag.)WO2016/138335; (2016); 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 69214-33-1 as follows. SDS of cas: 69214-33-1

Morpholine (2.0 ml, 23.2 mmol) was added to a stirred solution of a mixture 72/28 of 3-bromo-8-chloro-imidazo[l,2-a]pyrazine and 3,8-dibromo-imidazo[l,2-a]pyrazine (intermediate 15) (5.9 g, 11.6 mmol) and DIPEA (1.93 ml, 13.9 mmol) in ACN (54 ml). The mixture was stirred at 80 C for 7 h. and then the solvent was evaporated in vacuo. The crude product was dissolved in DCM and washed with a saturated solution of sodium carbonate. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 10/90). The desired fractions were collected and evaporated in vacuo and the crude product precipitated from Et20 to yield intermediate 26 (2.79 g, 85%) as a white solid.

According to the analysis of related databases, 69214-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose, Manuel; CONDE-CEIDE, Susana; MACDONALD, Gregor, James; PASTOR-FERNANDEZ, Joaquin; VAN GOOL, Michiel, Luc, Maria; MARTIN-MARTIN, Maria, Luz; VANHOOF, Greta, Constantia, Peter; WO2011/110545; (2011); 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. 1209646-17-2, name is 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

5-(4-(tert-butoxycarbonyl) piperazin-1 -yl) pyrazine-2-carboxylic acid (200 mg, 0.65 mmol), tert-butyl 2-amino-4-(thiophen-2-yl) phenylcarbamate (157 mg, 0.54 mmol) and EDCI (311 mg, 1.62 mmol) were added into Py (5 ml). The mixture was stirred at room temperature for overnight. When the reaction finished, it was concentrated and washed with Et20. The yellow solid was collected as product (310 mg, 65% yield).

According to the analysis of related databases, 1209646-17-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Regenacy Pharmaceuticals, LLC; van Duzer, John H.; Mazitschek, Ralph; (123 pag.)US2018/141923; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 78342-42-4, name is (S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine, 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 78342-42-4, HPLC of Formula: C9H16N2O2

To a solution of (25)-3,6-dimethoxy-2-(propan-2-yl)-2,5-dihydropyrazine (1.84 g, 9.99 mmol) in THF (50 mL) was added n-BuLi (6.0 mL, 2.5M in n-hexane) at -78 °C. The resulting solution was stirred for 30 mm at -78 °C. To this was added benzyl 4-[4-(bromomethyl)-2,3,5,6- tetrafluorophenyl]piperazine-1-carboxylate (4.60 g, 9.97 mmol) at -78 °C. The resulting solution was stirred for 2h at -78 °C. The reaction was then quenched by the addition of NH4C1 (sat., aq.) (40 mL). The resulting mixture was extracted with ethyl acetate (3 x 30 mL). The organic layers were combined, washed with brine (3 x 30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by reversed phase chromatography (Column: C18 silica gel; Mobile phase, A: water (containing 0.05percent TFA) and B: ACN (5percent to 75percent in 30 mm) to give benzyl 4-(4-[[(2R,55)-3,6-dimethoxy-5-(propan-2-yl)-2,5-dihydropyrazin-2-yl]methyl]-2, 3,5, 6-tetrafluorophenyl)piperazine- 1 -carboxylate as yellow oil. MS (ESI, m/z): 565 [M+H]t

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, (S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZABLOCKI, Mary-Margaret; GUERIN, David J.; NG, Pui Yee; WANG, Zhongguo; SHELEKHIN, Tatiana; CARAVELLA, Justin; LI, Hongbin; IOANNIDIS, Stephanos; (518 pag.)WO2019/32863; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

17231-51-5, name is 3-Amino-6-bromopyrazine-2-carbonitrile, 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. Safety of 3-Amino-6-bromopyrazine-2-carbonitrile

Step A Synthesis of 2-amino-3-cyano-5-(trimethylsilylethynyl)pyrazine as an intermediate A solution of 3.0 grams (0.015 mole) of 2-amino-3-cyano-5-bromopyrazine and 2.1 grams (0.021 mole) of trimethylsilylacetylene in 50 mL of acetonitrile is stirred, and 10.6 mL of triethylamine, 0.13 gram of copper iodide, and 0.29 gram of bis(triphenylphosphine)palladium(II) chloride are added in order. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about 20 hours. The reaction mixture is warmed to 70 C., where it is stirred for about 7.5 hours. After this time, the reaction mixture is concentrated under reduced pressure to a residue. The residue is dissolved in ethyl acetate, and the solution is washed with 50 mL of aqueous, dilute hydrochloric acid. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residue. The residue is subjected to column chromatography on silica gel. Elution is accomplished using tetrahydrofuran/methylene chloride combinations. The product-containing fractions are combined and concentrated under reduced pressure, yielding 2-amino-3-cyano-5-(trimethylsilylethynyl)pyrazine.

The synthetic route of 17231-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC Corporation; US5521190; (1996); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 87486-34-8, 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. 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2a-j (10 mmol, 1.0 eq) , 3,5-dibromo-1-methylpyrazin-2(1H)-one (2.95 g, 11 mmol, 1.1 eq) and DIEA (3.3 mL,20 mmol, 2.0 eq) in MeCN (20mL) was stirred at 80 °C for 5 hours. After cooling to room temperature, thesolvent was removed in vacuo, and the residue was purified using silica gelchromatography to give the title compounds, yield 72-85percent.

The synthetic route of 3,5-Dibromo-1-methylpyrazin-2(1H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Jianhong; Du, Jiatian; Huang, Chong; Wang, Tianqi; Huang, Luyi; Yang, Shengyong; Li, Linli; Bioorganic and Medicinal Chemistry Letters; vol. 29; 13; (2019); p. 1609 – 1613;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5521-55-1, 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 5521-55-1 as follows.

Step 5 4-[3-(4-Chloro-benzoylamino)-propoxy]-3-[3-(5-methyl-pyrazin-2-yl)-ureido]-benzoic acid ethyl ester 5-Methyl-pyrazine-2-carboxylic acid (0.5 g, 3 mmol) was heated in toluene (50 mL) with stirring. Diphenyl phosphoryl azide (DPPA) was added. The temperature was increased to 100 C. over 10 minutes and maintained for a further 15 minutes, until the evolution of gas had ceased. During this time, the solution changed colour from orange to dark red/brown. 3-Amino-4-[3-(4-chloro-benzoylamino)-propoxy]-benzoic acid ethyl ester (1.15 g, 3 mmol), in toluene (20 mL), was added via syringe at 100 C. and stirred for 30 minutes. The heat was removed and the reaction mixture was cooled to room temperature. The resulting precipitate was collected via filtration to give a white solid (888 mg, 58%). 1H NMR (400 MHz, DMSO-d6) delta 10.17 (s, 1H), 8.87 (s, 1H), 8.65 (s, 1H), 8.66 (s, 1H, broad), 8.17 (s, 1H), 7.86 (d, 2H), 7.65 (dd, 1H), 7.52 (d, 2H), 7.15 (d, 1H), 4.30 (q, 2H), 4.24 (t, 2H), 3.52 (m, 2H), 2.39 (s, 3H), 2.16 (m, 2H), 1.31 (t, 3H). LCMS: method A, Rt=3.33 min, [MH+=512].

According to the analysis of related databases, 5521-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2005/176733; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 123-32-0,Some common heterocyclic compound, 123-32-0, name is 2,5-Dimethylpyrazine, molecular formula is C6H8N2, 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.

2, 5-dimethylpyrazine (6 g, 55.6 mmol), carbon tetrachloride (50 mL) were added in a three-necked flask,After stirring, N-chlorosuccinimide (NCS) (7. 4 g, 55.6 mmol) and benzoyl peroxide(0. 05 g, 0.21 mmol),The reaction mixture was irradiated under incandescent light,Stir,Reflux reaction about 18h,TLC [V (ethyl acetate): V (petroleum ether) = 1: 2 as developing solvent] After the detection reaction is substantially complete,The reaction solution was cooled to 0 C,After standing for 1 hour,filter,The filter cake is washed with cold carbon tetrachloride,Combined filtrate and wash solution,Vacuum distillation of carbon tetrachloride,Get a light brown oil,Methylene chloride dissolved,After decolorization of activated carbon,Pale yellow oil,Without further direct reaction to the next step.

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

Reference:
Patent; Anhui University of Chinese Medicine; Hefei Industrial Pharmaceutical Institute Co., Ltd.; Li, JiaMing; He, GuangWei; Hu, MinHua; Huang, WeiJun; Zhu, Xiaoyu; Wang, Jie; Ye, WenFeng; Zhang, EnLi; (10 pag.)CN103664804; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem