Pyrazines

Application of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

(3-chloropyrazin-2-yl)methanamine.hydrochloride (20 g, 108 mmol) and trans-4-hydroxycyclohexanecarboxylic Acid (15.54 g, 108 mmol) EDCl.HCl (22.72 g, 119 mmol), 1-hydroxy-7-azabenzotriazole (7.33 g, 53.9 mmol) in dichloromethane (250 mL) was added triethylamine (23.96 mL, 172 mmol) and the reaction mixture was stirred at room temperature over night. The mixture was washed with 0.1 M HCl-solution, 5% NaHCO3, water and brine, dried over sodium sulfate and concentrated in vacuo. The product was purified using silica gel chromatography (dichloromethane/methanol = 9/1 v/v%) to give 31.1 g of (trans)-N-((3-chloropyrazin-2-yl)methyl)-4-hydroxycyclohexanecarboxamide (98%).

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

Reference:
Patent; MSD Oss B.V.; Man, de, Adrianus, Petrus, Antonius; Sterrenburg, Jan-Gerard; Raaijmakers, Hans C.A.; Kaptein, Allard; Oubrie, Arthur A.; Rewinkel, Johannes, Bernardus, Maria; Jans, Christiaan, Gerardus, Johannes, Maria; Wijkmans, Jacobus C.H.M.; Barf, Tjeerd A.; Gao, Xiaolei; Boga, Sobhana Babu; Yao, Xin; Zhu, Hugh Y.; Cooper, Allen B.; Kim, Ronald M.; EP2548877; (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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., Formula: C5H7Cl2N3

2-Chloro-3- aminomethylpyrazine.HCl (2 g; 11.1 mmol), (S)-(-)-1-(carbobenzyloxy)-2-piperidine carboxylic acid (3.2 g; 12.2 mmol) and N,N-diisopropylethylamine (7.7 mL; 44.4 mmol) were dissolved in dichloromethane (100 mL). HATU (6.3 g; 16.7 mmol) was added and the resulting mixture was stirred overnight at room temperature. The mixture was washed with aqueous sodium bicarbonate solution and water. The organic layer was then dried over sodium sulfate, filtered and evaporated to dryness. The crude material was chromatographed over SiO2 using a gradient of 20-80% ethyl acetate in heptane to give 4.4 g; 11.3 mmol of benzyl (2S)-2-[(3-chloropyrazin-2-yl)methylcarbamoyl]piperidine- 1-carboxylate as a colorless oil (73%).

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:
Article; Barf, Tjeerd; Covey, Todd; Izumi, Raquel; Van De Kar, Bas; Gulrajani, Michael; Van Lith, Bart; Van Hoek, Maaike; De Zwart, Edwin; Mittag, Diana; Demont, Dennis; Verkaik, Saskia; Krantz, Fanny; Pearson, Paul G.; Ulrich, Roger; Kaptein, Allard; Journal of Pharmacology and Experimental Therapeutics; vol. 363; 2; (2017); p. 240 – 252;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 24241-18-7, 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. 24241-18-7 name is 2-Amino-3,5-dibromopyrazine, 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.

5-Bromo-3-methoxypyrazin-2-amine A mixture of 3,5-dibromo-2-aminopyrazine (750 mg, 2.9 mmol), sodium methoxide (400 mg, 7.4 mmol) and methanol (20 ml) was refluxed for 16 h. The solvent was removed and the residue was purified using column chromatography. Yield: 450 mg 1H NMR (CDCI3): 3.99 (3H, s), 4.76 (2H, s), 7.63 (1H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-3,5-dibromopyrazine, and friends who are interested can also refer to it.

Reference:
Patent; MEDEIA THERAPEUTICS LTD; GOLDSTEINS, Gundars; KOISTINAHO, Jari; KOISTINAHO, Milla; RATILAINEN, Jari; PYSTYNEN, Jarmo; WO2014/68171; (2014); 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. 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, A new synthetic method of this compound is introduced below., Computed Properties of C9H11BrN2O3

Example 13-(2,2-Difluoro-2-phenylethylamino)-1-(ethoxycarbonylmethyl)-6- methylpyrazinoneA 2-liter, one-neck round bottom flask (equipped with a nitrogen inlet) was charged with 3-bromo-1 -(ethoxycarbonylmethyl)-6-methylpyrazinone (51.5 g, 0.187 mol), 2,2-difluoro-2-phenylethylamine (64.78 g, 0.412 mol), and toluene (450 ml). The reaction mixture was refluxed for 2 days and concentrated to yield a solid. The solid was triturated with ethanol-water (1 :1 , 890 ml) and the resulting mixture stirred for 2 h. The solid was collected by filtration and then washed with ethanol-water (1 :3, 450 ml), filtered, dried and to yield the title compound as a tan solid. MP: 106 – 1100C

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; JANSSEN PHARMACEUTICA, N.V.; WO2007/146553; (2007); A2;,
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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, A new synthetic method of this compound is introduced below., Safety of Methyl 2-aminopyrazine-3-carboxylate

Step 1 : Methyl S-amino–bromopyrazine-l-carboxylate[00210] A mixture of methyl 3-aminopyrazine-2-carboxylate (8.35 g, 54.53 mmol) and N- bromo-succinimide (9.705 g, 54.53 mmol) was stirred in MeCN (100 mL) at room temp overnight. The resultant precipitate was filtered, washed with MeCN and dried to give the desired product as a yellow solid (11.68 g, 92% Yield) 1H NMR (400.0 MHz, DMSO) 3.85 (s, 3H), 7.55 (br s, 2H) and 8.42 (s, IH) ppm; MS (ES+) 233

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; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-damien; DURRANT, Steven; KAY, David; O’DONNELL, Michael; KNEGTEL, Ronald; MACCORMICK, Somhairle; PINDER, Joanne; VIRANI, Anisa; YOUNG, Stephen; BINCH, Hayley; CLEVELAND, Thomas; FANNING, Lev, T.d.; HURLEY, Dennis; JOSHI, Pramod; SHETH, Urvi; SILINA, Alina; WO2010/54398; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 21279-62-9, The chemical industry reduces the impact on the environment during synthesis 21279-62-9, name is 3-Chloropyrazine-2-carboxamide, I believe this compound will play a more active role in future production and life.

General procedure: Compounds 1-6 were prepared according to conventional organic synthesis methods. 3-Chloropyrazine-2-carboxamide (1.27 mmol) was dissolved in THF (20 mL) in a round bottom flask and after that treated with two equivalents of the corresponding benzylamine and an equimolar amount of triethylamine. The reaction was conducted with continuous stirring and heating (70 C) under reflux in an oil bath for 15 h. Compounds 7-15 were synthesised using a microwave reactor with a focused field. 3-Chloropyrazine-2-carboxamide (1.27 mmol) was put into a thick-walled tube together with the corresponding benzylamine (2.54 mmol), pyridine (1.27 mmol), methanol (approx. 5 mL) and a magnetic stir bar and then sealed with a special cap. The reaction parameters were set according to the previously published paper as follows-140 C, 30 min, 200 W [29]. Reaction progress was checked by TLC (hexane:ethyl acetate-1:1). Regardless of the synthesis method used,all reaction mixtures were adsorbed on silica and subjected to preparative flash chromatography (hexane and ethyl acetate, gradient elution, detection wavelengths 260 nm and 280 nm). Products were recrystallized from ethanol or ethanol and water if necessary. All final substances were chemically characterized (1H-NMR, 13C-NMR, IR, melting point and elemental analysis).

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, 3-Chloropyrazine-2-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jandourek, Ondrej; Tauchman, Marek; Paterova, Pavla; Konecna, Klara; Navratilova, Lucie; Kubicek, Vladimir; Holas, Ondrej; Zitko, Jan; Dolezal, Martin; Molecules; vol. 22; 2; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 74290-65-6, These common heterocyclic compound, 74290-65-6, name is 3-Bromo-5-methylpyrazin-2-amine, 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.

A mixture of 3-bromo-5-methylpyrazin-2-amine (1 g, 5.3 mmol) in chloroacetaldehyde (5 mL) was heated to 100 C for 1 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulphate, filtered and concentrated to get residue. The residue was purified by flash chromatography using 20% ethyl acetate in hexanes to get pure titled compound (0.6 g, 53%). ?HNMR (300 MHz, DMSO- d6): oe 8.40 (d, J = 0.9 Hz, 1H), 8.02 (d, J = 0.6 Hz, 1H), 7.79 (d, J =0.9 Hz, 1H), 2.37 (s, 3H).

Statistics shows that 3-Bromo-5-methylpyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 74290-65-6.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; KOTRABASAIAH UJJINAMATADA, Ravi; PANDIT, Chetan; (152 pag.)WO2016/185342; (2016); 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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H4BrN3

A method for preparing methyl (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate, comprising the steps of: (1) using 5-bromo-4,7-diazaindene as raw material,Reacting with the prepared 20% ammonia water at a temperature of 140 C and a pressure of 3 MPa,The molar ratio of 5-bromo-4,7-diazaindene to ammonia water is 1:12. A cuprous chloride/ferrous chloride composite catalyst is added to the reaction system, and the molar ratio of cuprous chloride to ferrous chloride is 1:1, and the total amount of the catalyst is2% by mass of 5-bromo-4,7-diazepine, the reaction gives compound 1;

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; Nanjing Xin Meihe Pharmaceutical Technology Co., Ltd.; Zhou Wenbin; Yang Yuanming; Wang Zhengxi; (6 pag.)CN110105363; (2019); 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. 4774-14-5, name is 2,6-Dichloropyrazine, A new synthetic method of this compound is introduced below., SDS of cas: 4774-14-5

Aniline (265.7 mg, 2.85 mmol) and 2,6-dichloropyrazine (427.2 mg, 2.87 mmol) were dissolve in n-butanol (2.0 mL), and 4.0 M hydrochloric acid in 1,4-dioxane (2 mL) was added. The mixture was heated to 120 C for 96 h, poured in water (30 mL), extracted with ethyl acetate (30 mL), the organic layer was washed with saturated aqueous sodium bicarbonate solution (30 mL) and brine (25 mL), concentrated and purified by chromatography (30 g silica gel, 0.5-1.0% ethyl acetate-dichloromethane) to afford 6-chloro-N-phenylpyrazin-2-amine (225.9 mg, 38% yield) as a dark yellow semi-solid; 1H NMR (400 MHz, CDCl3): delta 8.10 (s, 1H), 7.97 (s, 1H), 7.40-7.35 (m, 4H), 7.17-7.12 (m, 1H), 6.74 (s, 1H); Calcd mass for C10H8ClN4: 205.04; LRMS (ESI) m/z [M+H]+ = 206.20.

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:
Article; Kashyap, Sudhir; Sandler, Joel; Peters, Ulf; Martinez, Eduardo J.; Kapoor, Tarun M.; Bioorganic and Medicinal Chemistry; vol. 22; 7; (2014); p. 2253 – 2260;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19745-07-4, name is 2,5-Dichloropyrazine, 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 19745-07-4, Product Details of 19745-07-4

N-ethyl piperidin-4-ol(200 mg1.55 mmol) was added to dry THF (10 mL) and the mixture was cooled to 0oC, then NaH (60percent, 124 mg3.1 mmol) was added slowly. The mixture was stirred at 0oC for 0.5 h and then 2,5-dichloropyrodazine(231 mg1.55 mmol) was added and stirred overnight. The reaction was quenched with iced water and extracted with DCM, the organic layer was washed with brine, dried and concentrated to afford compound 12(330 mg, white solid).LC-MS: 242.1(M+H).

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, 2,5-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fu, Yan; Tang, Shuai; Su, Yi; Lan, Xiaojing; Ye, Yan; Zha, Chuantao; Li, Lei; Cao, Jianhua; Chen, Yi; Jiang, Lei; Huang, Ying; Ding, Jian; Geng, Meiyu; Huang, Min; Wan, Huixin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5332 – 5336;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem