Month: June 2021

33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, 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. name: Methyl 5-chloropyrazine-2-carboxylate

A mixture of 3-Cyclopentyl-7- (4-piperidinyl)-2, 3,4, 5-tetrahydro-1 H-3-benzazepine (product of E230, step 2) (0.5g, 1. 68mol), potassium carbonate (0.46g, 3. 35mmol) and methyl 5- chloro-2-pyrazinecarboxylate (0.58g, 3. 35mmol) in dimethylformamide (20ml) was heated at 90C for 3 hours. The crude mixture was purified on an SCX ion exchange cartridge eluting with methanol and then 2M ammonia in methanol. The basic fractions evaporated and the residue purified by column chromatography on silica eluting with 95-5 dichloromethane-2M ammonia in methanol to afford the title compound as a yellow solid (0.55 g, 75%) MS (AP+) m/e 435 [M+H] +.

The synthetic route of 33332-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/87746; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference 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.

A mixture of (cis)-2-((benzyloxy)carbonyl)-4-oxooctahydro-l H-pyrido [1,2- a]pyrazine-7-carboxylic acid (0.7 g, 2.1 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (450 mg, 2.5 mmol), HATU (1.2 g, 3.1 mmol) and TEA (0.85 g, 8.4 mmol) in DMF (10 mL) was stirred at 25 C for overnight. Then the reaction mixture was poured into water, the mixture was extracted with EA (50 mix 3). The combined organic phase was washed with brine (100 mL), dried over Na2S04, concentrated in vacuo, the residue was purified by silica gel column chromatography (PE/THF = 1/3) to give (cis)-benzyl 7-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-4-oxohexahydro-lH- pyrido[l,2-a]pyrazine-2(6H)-carboxylate (440 mg, yield 45.8 %).

The synthetic route of 939412-86-9 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

117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, 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. Quality Control of 5-Bromo-3-morpholinopyrazin-2-amine

Preparation of Intermediate I-35. Intermediate I-02 (2 g, 7.72 mmol) and methyl 4-chloroacetoacetate (3.56 mL, 30.88 mmol) were heated in two sealed tubes (half of material in each tube) at 90 C. for 2 h. Volatiles were removed under reduced pressure and the residue was purified by flash chromatography on silica gel (c-Hex/EtAOAc 10:0 to 6:4) to obtain a solid that was washed with diethyl ether to render the desired product I-35 (1.17 g, Y: 49%).

The synthetic route of 117719-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Centro Nacional De Investigaciones Oncologicas (CNIO); US2012/83492; (2012); 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. 21279-62-9, name is 3-Chloropyrazine-2-carboxamide, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Chloropyrazine-2-carboxamide

General procedure: The starting compound (1.27 mmol) was treated with 18 aliphatic amines, alicyclic amines or saturated heterocycles containing at least one nitrogen atom (2.54 mmol). Four reactions were completed by conventional heating methods. The conditions were 110 C, toluene as a solvent and pyridine (1.27 mmol) as a base. The reaction time was set to one hour. Then the reactions were completed using the microwave reactor with focused field and conditions used for syntheses were 140 C, 30 min,120 W, methanol used as a solvent and pyridine (1.27 mmol) as a base. They were set experimentally with respect to prior experience. The progress of reaction was monitored with TLC in system hexane/ethyl acetate (1:1). Then the mixture was separated by flash column chromatograph using gradient elution. Mobile phases were hexane and ethyl acetate again.

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; Jandourek, Ondrej; Dolezal, Martin; Kunes, Jiri; Kubicek, Vladimir; Paterova, Pavla; Pesko, Matus; Buchta, Vladimir; Kralova, Katarina; Zitko, Jan; Molecules; vol. 19; 7; (2014); p. 9318 – 9338;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, 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 875781-43-4, Computed Properties of C6H4BrN3

2.1 1.66 g (2.37 mmol) of bis(triphenylphosphine)palladium dichloride and 16.8 g (80 mmol) of 1-methyl-1H-pyrazole-4-boronic acid pinacol ester are added successively to a solution, kept under nitrogen, of 9.4 g (47.0 mmol) of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (prepared in two steps from 3,5-dibromopyrazin-2-amine in accordance with WO2006/15124 or WO2010/68483) in 400 ml of dioxane, and the mixture is stirred at room temperature for 5 minutes. 94 ml of a 2 M aqueous sodium carbonate solution are then added. The mixture is heated to 90 C. and kept at this temperature for 2 hours. The reaction mixture is cooled to room temperature and partitioned between water and ethyl acetate. The combined organic phases are dried over sodium sulfate and evaporated. The residue is boiled in tert-butyl methyl ether, cooled and filtered off with suction. The residue is dried in vacuo: 2-(1-methyl-11H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine as orange crystals; HPLC/MS: 1.30 min, [M+H] 200.

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; MERCK PATENT GMBH; Dorsch, Dieter; Wucherer-Plietker, Margarita; Mueller, Thomas J.J.; Merkul, Eugen; US2013/217951; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 912773-24-1, The chemical industry reduces the impact on the environment during synthesis 912773-24-1, name is 6-Bromoimidazo[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

To a solution of 6-bromoimidazo [1,2-a]pyrazine (1.43 g, 7.26 mmol, 1.0 equiv) in DMF (50 mL) was added NBS (1.39 g, 7.81 mmol, 1.1 equiv) at -5~0 C. The resulting solution was stirred at 0 C for 1 hr. The resulting mixture was diluted with ethyl acetate (300 mL) then washed with brine. The organic layer was dried and concentrated to obtain 1.8 g of the crude product as a white solid. (ES, m/z): [M + H+] 278; H-NMR (300 MHz, CDCI3): 5 8.92 (d, J= 1.2 Hz, 1H), 8.28 (s, 1H), 7.84 (d, J= 1.2 Hz, 1H).

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, 6-Bromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; NOVARTIS AG; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; PARASELLI, Prasuna; LEONG, Seh Yong; ROLAND, Jason Thomas; MISHRA, Pranab Kumar; YEUNG, Bryan KS; ZOU, Bin; WO2014/78813; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 939412-86-9, 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 939412-86-9 as follows.

Step-2: (0932) Preparation N-((3-chloropyrazin-2-yl)methyl)acetamide: (0933) [00353] To a solution of (3-chloropyrazin-2-yl)methanamine hydrochloride (3.5 g, 19.49 mmol) in dichloromethane (100 mL) was added diisopropylethylamine (10.18 mL, 38.99 mmol) followed by acetic anhydride (3.67 mL, 38.9 mmol) at room temperature. Then the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ice water (100 mL), basified with saturated sodium bicarbonate solution and extracted with ethyl acetate (3 x 200 mL). The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated. The crude product was purified by silica gel column chromatography using 3% methanol in dichloromethane to afford the title compound N-((3- chloropyrazin-2-yl)methyl)acetamide (1.66 g, 46% yield) as a brown solid. Calculated (M+H): 186.0; Found (M+H): 186.1.

According to the analysis of related databases, 939412-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1208082-91-0, name is 6,8-Dibromo-2-methylimidazo[1,2-a]pyrazine, 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 1208082-91-0, Quality Control of 6,8-Dibromo-2-methylimidazo[1,2-a]pyrazine

A mixture of Intermediate 1-05 (1.75 g, 6.015 mmol), morpholine (0.526 mE, 6.015 mmol) and DCM (20 mE) was stirred at rt for 16 h. Additional morpholine (0.52 6 mE,6.015 mmol) was added and the mixture was stirred at rt for18 h more. Na2CO3 sat. aq. was added. The organic phase was separated, dried (Na2SO4), filtered and evaporated till dryness to obtain 1.8 g of intermediate 1-10 (Y: quantitative). The resulting product was used in the next step without further purification.

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; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); Serrano Marugan, Manuel; Pastor Fernandez, Joaquin; Martinez Gonzalez, Sonia; Ortega Molina, Ana; Bischoff, James R.; Oyarzabal Santamarina, Julen; (220 pag.)US9993554; (2018); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 54608-52-5, The chemical industry reduces the impact on the environment during synthesis 54608-52-5, name is 2-Hydrazinopyrazine, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 2-hydrazinylpyridine (2, 0.5?mmol) in EtOH (5?mL) was added the corresponding isothiocyanate (3, 0.6?mmol) slowly at room temperature. After the total consumption of the substrate 2 (indicated by TLC), the reaction mixture was treated with iodine (140?mg, 0.55?mmol) and K2CO3 (138?mg, 1?mmol) in sequence, and then stirred at room temperature until TLC indicated the disappearance of the addition intermediate 4. Upon the completion of the reaction, it was quenched with 5% Na2S2O3 (5?mL), diluted with brine (10?mL) and then extracted with CH2Cl2 (enriched 5% MeOH, 4?*?10?mL). The combined organic layer was dried over anhydrous Na2SO4, concentrated, and then purified through silica gel column chromatography using a mixture of EtOAc/petroleum ether (PE) or MeOH/EtOAc as the eluent to afford the product 1.

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-Hydrazinopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jiao, Shufeng; Wang, Zhen; Zhao, Qiongli; Yu, Wenquan; Chang, Junbiao; Tetrahedron; vol. 74; 24; (2018); p. 3069 – 3073;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1053656-22-6, name is 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, 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 1053656-22-6, Recommanded Product: 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate

To a chloroform solution (250 ML) of ethyl 7- (TERT-BUTOXYCARBONYL)-5, 6,7, 8- tetrahydroimidazo [1, 2-a] pyrazine-2-carboxylate from Example 10, Step A (18.4 g, 94 mmol), bromine (45 g, 281 mmol) was added, and the mixture was stirred at room temperature for an hour. An aqueous solution of sodium bisulfite was then added and the product was extracted with two 100-ML portions of dichloromethane. The combined organic extracts were washed sequentially with sodium bicarbonate and brine, then dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, gradient elution, 50% ethyl acetate/hexane to 100% ethyl acetate) to give the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2004/58266; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem