Month: June 2021

Synthetic Route of 36070-79-8,Some common heterocyclic compound, 36070-79-8, name is 6-Chloropyrazine-2-carboxamide, molecular formula is C5H4ClN3O, 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: 150 mg (0.952 mmol) of 5-Cl-PZA (1) or 6-Cl-PZA (2) was dissolved in ethanol together with triethylamine (1 eq., 96 mg, 0.952 mmol). Three equivalents of corresponding alkylamine were added to the reaction mixture and refluxed in ethanol generally for 6 hours. The completion of the reaction was checked by TLC chromatography (eluent: hexane/ethyl acetate, 1:2). The crude product was absorbed on silica by solvent evaporation and purified by flash chromatography (hexane/ethyl acetate gradient elution).

The synthetic route of 36070-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Servusova, Barbora; Paterova, Pavla; Mandikova, Jana; Kubicek, Vladimir; Kucera, Radim; Kunes, Jiri; Dolezal, Martin; Zitko, Jan; Bioorganic and Medicinal Chemistry Letters; vol. 24; 2; (2014); p. 450 – 453;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 54013-07-9, 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. 54013-07-9 name is 5-Methoxypyrazin-2-amine, 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.

Example 1AX; Preparation of 2-ethyl-N-(5-methoxypyrazin-2-yl)-4-f4- (methylsulfonyl)phenoxyl-2H-indazole-6-carboxamide (1AX): To a solution of 5-methoxypyrazin-2-annine (167 mg, 1.34 mmol) in dry dichloroethane (2.0 ml_) was added dimethylaluminum chloride (2.67 ml_, 2.67 mmol) slowly at O0C under nitrogen. After addition, the mixture was stirred for 1 hour at room temperature and then added methyl 2-ethyl-4-(4- (methylsulfonyl)phenoxy)-2H-indazole-6-carboxylate (1-1 f-7,100.0 mg, 0.267 mmol). Then the mixture was heated to 60-700C overnight. The reaction mixture was cooled to room temperature, poured into potassium sodium tartrate (aq., 10 ml_), and extracted with ethyl acetate (10 ml_ 3 times). The combined organic layers were dried and concentrated under reduced pressure and purified by preparative HPLC to afford the title compound (1AX, 20.0 mg, yield: 16%) as a white solid.1H NMR (400 MHz, DMSO-d6): delta 1.46-1.49 (t, 3H), 3.15 (s, 3H), 3.88 (s, 3H), 4.43-4.49 (q, 2H), 7.20 (s, 1 H), 7.17-7.31 (d, 2H), 7.91 -7.93(d, 2H), 8.15(s, 1 H), 8.32(s, 1 H), 8.44 (s, 1 H), 8.88 (s, 1 H), 10.97 (s, 1 H). MS (M+1 ): 468.2.

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

Reference:
Patent; PFIZER INC.; CORBETT, Jeffrey Wayne; GUZMAN-PEREZ, Angel; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/103438; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-28-4, A common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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.

Synthesis 2-1 -B 5-bromo-6-chloropyrazin-2-amine 6-Chloropyrazin-2-amine (2.50 g, 19.3 mmol) was stirred in dichloromethane (60 mL) and cooled to O°C. N-Bromosuccinimide (2.92 g, 16.4 mmol) was added slowly and the reaction mixture was stirred at 0°C for 60 minutes. The reaction mixture was filtered through celite and concentrated to give a brown oil. Purification by flash chromatography, eluting with 0-25percent ethyl acetate-hexane, gave the title compound as a yellow solid (1.69 g, 8.16 mmol, 42percent). 1HMR (d6-DMSO, 400 MHz) delta 7.65 (s, 1H), 7.1 (br s, 2H). LC-MS (1) rt 1.46 min; m/z (ESI-) 205 (M-H).

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; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/103966; (2009); 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 6966-01-4 as follows. Product Details of 6966-01-4

To a solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (100 mg, 0.43mmol) in MeOH (5 mL) was added 2 mL of NaOH aqueous solution (5 N). After being stirred at50C for 4 h, the mixture was cooled and acidified with 1 M HC1 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%). ?H-NMR (DMSO-d6, 400 MHz) 8.38 (s, 1H), 7.517.56 (m, 2H). MS (M+H): 218 / 220.

According to the analysis of related databases, 6966-01-4, the application of this compound in the production field has become more and more popular.

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; WO2014/205593; (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. 56423-63-3, name is 2-Bromopyrazine, A new synthetic method of this compound is introduced below., SDS of cas: 56423-63-3

Example 88CPreparation of Compound (95c) A mixture of compound (95b) (1.70 g), K2CO3 (1.87 g, 4 equiv.), Pd(Ph3P)2Cl2 (72.0 mg, 3%), and 2-bromopyrazine (1.07 g, 2 equiv.) in dioxane (18 mL) and H2O (6 mL) was degassed within an ultrasonic cleaner for 1 hr under argon protection. The mixture was heated at reflux with stirring for 3 hr. The residue was partitioned with EtOAc (80 mL) and H2O (30 mL). The EtOAc layer was washed with brine, dried on MgSO4 and purified through FCC (EtOAc/Hexanes=1/1) to give 1.5 g of compound (95c).

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; BIOMARIN PHARMACEUTICAL INC.; US2011/178065; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6966-01-4, 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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To the solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (10.0 g 43.1 mmol) in MeOH (70 mL) was added a solution of Li OH (9.0 g, 215 mmol) in water (70 mL). The mixture was stirred at 90 C for 3 hours. The reaction mixture was cooled to rt and acidified to PH = 4-5 with HC1 (2 M). The mixture was filtered to afford 7.4 g of 6 (79 %) as yellow solid. (0170) [0033] LC-MS (M+l): 218.0; 1H MR (400 MHz, DMSO-d6) delta 8.39 (s, 1H), 7.59 (br, 2H).

The chemical industry reduces the impact on the environment during synthesis Methyl 3-amino-6-bromopyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERRIMACK PHARMACEUTICALS, INC.; DRUMMOND, Dary| C.; GENG, Bolin; KIRPOTIN, Dmitri B.; TIPPARAJU, Suresh, K.; KOSHKARYEV, Alexander; ALKAN, Ozan; (142 pag.)WO2017/123588; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 24241-18-7, 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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of Intermediate tert-butyl (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate Step A: 3,5-dibromopyrazin-2-amine to 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine [0183] To a solution of 3,5-dibromopyrazin-2-amine (125 g, 494 mmol), TEA (207.0 mL, 1483 mmol), and copper (I) iodide (0.941 g, 4.94 mmol) in THF (1255 mL) is added PdCl2(PPh3)2 (3.47 g, 4.94 mmol). The reaction mixture is cooled at about -5-0 C. and a solution of (trimethylsilyl)acetylene (65.0 mL, 470 mmol) in THF (157 mL) is added dropwise over about 15 min. The reaction mixture is stirred at about -5-0 C. for about 1.5 h and then allowed to warm to room temperature (RT) overnight. The reaction mixture is then filtered through a CELITE pad and washed with THF until no further product eluted. The filtrate is concentrated under reduced pressure to give a brown-orange solid. The solid is triturated and sonicated with warm petroleum ether (b.p. 30-60 C., 400 mL), cooled to RT, collected, washed with petroleum ether (b.p. 30-60 C.; 2×60 mL), and dried to give 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine (124 g, 93%, 93% purity) as a brown solid: LC/MS (Table 1, Method b) Rt=2.51 min; MS m/z: 270, 272 (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-Amino-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; Voss, Jeffrey W.; Camp, Heidi S.; Padley, Robert J.; US2015/118229; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 23688-89-3, 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. 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

2-Phenoxyaniline (0.185 g, 1.0 mmol), 6-chloropyrazine-2-carboxylic acid (0.158 g, 1.0 mmol) and 30 mL of dichloromethane were added to the reaction flask, and Et3N (0.202 g, 2.0 mmol) was added. Then, EDCI (0.287 mg, 1.5 mmol), HOBt (0.20 g, 1.5 mmol) was added, and the reaction was carried out at 25 C for 2.5 hours. The reaction was completed by TLC, and the reaction was completed. The reaction mixture was washed twice with water and once with saturated brine. The organic phase is dried over anhydrous sodium sulfate, de-solued to give a crude product, and recrystallized from ethanol.Brick red solid, m.p. 138-140 C, yield 79.0%

The chemical industry reduces the impact on the environment during synthesis 6-Chloropyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chen Lei; (6 pag.)CN108997228; (2018); 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. 1082843-70-6, name is 3,5-Dibromo-2-chloropyrazine, A new synthetic method of this compound is introduced below., name: 3,5-Dibromo-2-chloropyrazine

Step 2: Synthesis of Compound (B’) as Described in the General Reaction Scheme; 3-chloro-6-bromopyrazin-2-yl Amine Compound A’ described in the previous step (9.5 g, 37.55 mmol) is suspended in concentrated NH4OH (60 mL) and the resulting mixture is heated in a pressure autoclave to 80 C., typically overnight. The vessel is then allowed to cool down to room temperature slowly, and is then further cooled in an ice bath, causing the precipitation of the desired material. The solid is separated by filtration, washed with cyclohexane, to afford after drying, the title compound B’ (5 g) as a 83/17 mixture of regiosiomers. The mixture is then purified by column chromatography. M+H+, m/z=209

The synthetic route of 1082843-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Andrews, Martin James Inglis; Chambers, Mark Stuart; Van De Poel, Herve; Bar, Gregory Louis Joseph; US2009/286798; (2009); 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. 21279-64-1, name is 5-Chloropyrazine-2-carboxamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Chloropyrazine-2-carboxamide

General procedure: 150 mg (0.952 mmol) of 5-Cl-PZA (1) or 6-Cl-PZA (2) was dissolved in ethanol together with triethylamine (1 eq., 96 mg, 0.952 mmol). Three equivalents of corresponding alkylamine were added to the reaction mixture and refluxed in ethanol generally for 6 hours. The completion of the reaction was checked by TLC chromatography (eluent: hexane/ethyl acetate, 1:2). The crude product was absorbed on silica by solvent evaporation and purified by flash chromatography (hexane/ethyl acetate gradient elution).

According to the analysis of related databases, 21279-64-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Servusova, Barbora; Paterova, Pavla; Mandikova, Jana; Kubicek, Vladimir; Kucera, Radim; Kunes, Jiri; Dolezal, Martin; Zitko, Jan; Bioorganic and Medicinal Chemistry Letters; vol. 24; 2; (2014); p. 450 – 453;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem