Month: June 2021

Electric Literature of 313339-92-3, 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 313339-92-3 as follows.

Into a 25-mL round-bottom flask, was placed 3,5-dichloropyrazine-2-carbonitrile (450 mg, 2.59 mmol, 1.00 equiv), and acetic acid (10 mL), followed Raney Ni (50 mg) tfc was introduced into the reaction mixture. The resulting solution was stirred overnight at 50 C in an oil bath. The solid was filtered out and the resulting mixture was concentrated under vacuum to give 560 mg (crude) of 9-2 as a green solid

According to the analysis of related databases, 313339-92-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; BECK, Hilary, Plake; GONZALEZ-LOPEZ, Marcos; SUTTON, James, Clifford, Jr.; (86 pag.)WO2019/156989; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 939412-86-9, These common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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.

2a. Synthesis of N-((3-chloropyrazin-2-yl)methyl)-4-oxocyclohexanecarboxamide To a stirred suspension of 2-aminomethyl-3-chloropyrazine hydrochloride (3.89 mmol, 0.70 g) in dichloromethane (25 mL) at room temperature was subsequently added triethylamine (7.78 mmol, 1.08 mL), 0-(7-azabenzotriazol-1-yl)-1 ,1 ,3,3-tetramethyluroniumhexafluorophosphate (4.67 mmol, 1.77 g) and finally 4-oxocyclohexanecarboxylate (3.89 mmol, 553 mg). After stirring for 16 hours, the suspension filtered over decalite. The decalite was washed with dichloromethane. The filtrate was washed with water, dried (sodium sulfate) and concentrated in vacuo. The resulting crude product was purified by column chromatography on silica gel (ethyl acetate). The product was dissolved in dichloromethane, washed with water and concentrated in vacuo to afford 1.09 g of the title compound.H NMR (CDCl3, 400 MHz): delta 2.03 – 2.14 (m, 2H), 2.22-2.30 (m, 2H), 2.35 – 2.45 (m, 2H), 2.52 – 2.60 (m, 2H), 2.68 – 2.78 (m, 1 H), 4.73 (d, J = 4 Hz, 2H), 6.93 (brs, 1 H), 8.34 – 8.37 (m, 1 H), 8.46 (d, J = 2 Hz, 1 H).

Statistics shows that (3-Chloropyrazin-2-yl)methanamine hydrochloride is playing an increasingly important role. we look forward to future research findings about 939412-86-9.

Reference:
Patent; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, 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 16298-03-6, Product Details of 16298-03-6

Example 1 : 5-Amino-6-(6-methyl-lH-benzimidazol-2-yl)-N-(tetrahydrofuran-2- ylmethyl)pyrazine-2-carboxamide (Compound 11-52)SCHEME IMETHOD A:Step 1: Methyl 3-amino-6-bromopyrazine-2-carboxylate[00139] 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 ambient temperature overnight. The resultant precipitate was filtered, washed with MeCN and dried to give the desired product as a yellow solid (1 1.68 g, 92% Yield)XH NMR (400.0 MHz, DMSO) delta 3.85 (s, 3H), 7.55 (br s, 2H) and 8.42 (s, 1H) ppm; MS (ES+) 233.0

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, Methyl 2-aminopyrazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; KNEGTEL, Ronald, Marcellus, Alphonsus; O’DONNELL, Michael; REAPER, Philip, Michael; WO2011/143419; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 873-42-7,Some common heterocyclic compound, 873-42-7, name is 2-Amino-3,5-dichloropyrazine, molecular formula is C4H3Cl2N3, 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 the solution of 229 (100 mg, 0.39 mmol) in dried THF (10mL) was added t-BuOK (44 mg, 0.39 mmol) . The mixture was stirred at room temperature for 10min, then was added 2-nitro-3-fluoro-5-chloropyridine (69 mg, 0.39 mmol) and continued to stirred at room temperature for 1h. The reaction was quenched with silica gel (1g) , and purified by column chromatography to give the desired product (153 mg, 95%) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-3,5-dichloropyrazine, its application will become more common.

Reference:
Patent; FUJIAN HAIXI PHARMACEUTICALS CO., LTD; FENG, Yan; WANG, Ruyong; LI, Junqing; ZHENG, Jianjia; LIAN, Xin; GONG, Xuan; FU, Yueli; KANG, Xinshan; (144 pag.)WO2019/174601; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 122-05-4, 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. 122-05-4, name is Pyrazine-2,5-dicarboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a mixture of tris(2-pyridylmethyl)amine, TPA (0.146g, 0.50mmol) and Cu(ClO4)2·6H2O (0.109g, 0.50mmol) dissolved in MeOH (20mL), 2,3-pyrazine-dicarboxylic acid (H2Pyaz2,3-dc) (0.054g, 0.25mmol) which was neutralized with LiOH (0.012g, 0.5mmol) dissolved in 5.0mL H2O was added drop by drop. The resulting solution was heated for 5min on a steam-bath, filtered through Celite and then was allowed to stand at room temperature. The resulting precipitate, which was obtained after four days was collected by filtration and recrystallized from H2O to produe aqua blue single crystals of X-ray quality. These were collected by filtration, washed with propan-2-ol, Et2O and dried in air. (overall yield: 62mg, 25% based on H2Pyaz2,3-dc)

The synthetic route of Pyrazine-2,5-dicarboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Massoud, Salah S.; Louka, Febee R.; Gazzaz, Mohammed A.; Henary, Maher M.; Fischer, Roland C.; Mautner, Franz A.; Polyhedron; vol. 111; (2016); p. 45 – 52;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6863-74-7, name is 6-Chloropyrazine-2-carbonitrile, 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 6863-74-7, Application In Synthesis of 6-Chloropyrazine-2-carbonitrile

Reference Example 106 tert-Butyl [methyl(6-cyano-2-pyrazinyl)amino]acetate 2-Chloro-6-cyanopyrazine (2.09 g, 15.0 mmol), sarcosine tert-butyl ester hydrochloride salt (2.72 g, 15.0 mmol) and triethylamine (2.38 ml, 17.0 mmol) were added to DMF (30 ml), and the mixture was stirred at room temperature for 18 hrs.. The reaction mixture was combined with ethyl acetate and water.. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.. The solvent was evaporated to give the titled compound (1.00 g, 27 %) as pale yellow crystals.1H-NMR (CDCl3) delta: 1.46 (9H, s), 3.21 (3H, s), 4.18(2H, s), 8.16 (1H, s), 8.23 (1H, s). IR(KBr): 2233, 1734, 1576, 1521, 1419, 1367, 1226, 1153, 993, 842 cm-1.

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; Takeda Chemical Industries, Ltd.; EP1424336; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, 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 76537-18-3, category: Pyrazines

Step 1: 5-Chloro-3-((trimethylsilyl)ethynyl)pyrazin-2-amineTo a 500 mL round-bottomed flask was added 3-bromo-5-chloropyrazin-2-amine (5 g, 23.99mmol), ethynyltrimethylsilane (10.17 ml, 72.0 mmol), and triethylamine (33.4 ml, 240 mmol)in THF (100 ml) to give a brown solution. The reaction was degassed and purged withnitrogen. To the stirring solution was added bis(triphenylphosphine)palladium(ll) chloride (1.684g, 2.399mmo1) and copper(l) iodide (914mg, 4.8Ommol). The reaction was stirred at room temperature for 30mins. The reaction was extracted into ethyl acetate, washed with brine, the organic layer separated, dried over Mg504, filtered and the solvent removed underreduced pressure. The crude product loaded onto silica was purifiied by flash column chromatography elution with iso hexane:ethyl acetate (0-30%) using an 80g silca cartridge. The required fractions were combined and the solvent removed under reduced pressure to yield a brown solid;LCMS: Rt = 1 .29mins MS mlz 226.2 [M+H]+; Method 2minLowpHvo2.1H NMR (400MHz, DMSO-d6) O 8.08 (1H, 5), 6.82 (2H, broad 5), 0.27 (9H, 5).

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-Bromo-5-chloropyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; (395 pag.)WO2015/162459; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 59303-10-5, 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. 59303-10-5, name is 2-Chloro-5-methylpyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-((lr,4r)-4-(4-(methylsulfonyl)phenoxy)cyclohexyloxy)piperidine hydrochloride (24.2 mg, 0.062 mmol), 2-chloro-5-methylpyrazine (90 mg, 0.700 mmol), and triethylamine (40 mu, 0.287 mmol) in iPrOH (1 mL) was heated under microwave irradiation at 200 C for 5 h. The mixture was concentrated and the residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (8.7 mg) as a white solid. LCMS m/z = 446.2 [M+H]+; .H NMR (400 MHz, CDC13) delta 1.46-1.68 (m, 6H), 1.89-1.96 (m, 2H), 1.99- 2.04 (m, 2H), 2.10-2.15 (m, 2H), 2.39 (s, 3H), 3.03 (s, 3H), 3.21-3.27 (m, 2H), 3.55-3.59 (m, IH), 3.63-3.67 (m, IH), 3.91-3.97 (m, 2H), 4.39-4.44 (m, IH), 6.98-7.01 (m, 2H), 7.83-7.86 (m, 2H), 7.94 (s, IH), 8.07 (s, IH).

The synthetic route of 2-Chloro-5-methylpyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; BUZARD, Daniel J.; LEHMANN, Juerg; NARAYANAN, Sanju; YUE, Dawei; WO2011/127051; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 32974-92-8, The chemical industry reduces the impact on the environment during synthesis 32974-92-8, name is 1-(3-Ethylpyrazin-2-yl)ethanone, I believe this compound will play a more active role in future production and life.

1) 2-acetyl-3-ethylpyrazine (420 ul, 3 mmol) was dissolved in methanol (20 ml).After dissolution,Add thiosemicarbazide (273 mg, 3 mmol),well mixed,The mixed solution was refluxed at 65 C for 4 h.filter,The filtrate evaporates at room temperature.There is a pale yellow crystal,Filter again,Wash 2-3 times with absolute ethanol,Obtaining a ligand L1;

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, 1-(3-Ethylpyrazin-2-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangxi Normal University; Yang Feng; Sun Zewen; Zhao Lei; Liang Hong; (16 pag.)CN109796501; (2019); A;,
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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H3ClN2O2

5-Chloropyrazine-2-carboxylic acid [CAS RN: 36070-80-1] (420 mg, 2.65 mmol,1.0 eq) was dissolved in 10 mL THF, and CDI (430 mg, 2.65 mmol, 1.0 eq) was added. Then, the reaction mixture was heated to 75C for 45 mm. On cooling the resulting solution was added dropwise to a solution of tert-butyl methyl[2- (methylamino)ethyl]carbamate [CAS-RN: 112257-19-9] (513 mg, 2.73 mmol,1.03 eq) in 3 mL THF. The reaction mixture was stirred at 70C for 60 mm. Thevolatile components were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane -> hexane/ethyl acetate 2/1 -> hexane/ethyl acetate 2/3) to give 322 mg (37% yield of theory) of the title compound.UPLC-MS (Method 1): R = 1 .07 mm; MS (EI0): m/z = 329 [M+H].

According to the analysis of related databases, 36070-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem