Month: July 2021

Some common heterocyclic compound, 5049-61-6, name is Pyrazin-2-amine, molecular formula is C4H5N3, 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. Product Details of 5049-61-6

To a solution of pyrazin-2-amine (30 g, 0.32 mmol) in DCM (900 mL) at 0 C was added NBS (56 g, 0.32 mmol). The reaction mixture was stirred at ambient temperature for 3 h and then washed with sat. NaHCO3 and brine. The organic layer was dried over anhydrous Na2504, filtered and concentrated to afford 5 -bromopyrazin-2-amine (38 g, 70 %) as a white solid whichwas used directly in 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 5049-61-6, its application will become more common.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BRAMELD, Kenneth A.; VERNER, Erik; WO2014/182829; (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. 4858-85-9, name is 2,3-Dichloropyrazine, A new synthetic method of this compound is introduced below., name: 2,3-Dichloropyrazine

A suspension of 2,3-dichloropyrazine (3.5 g, 0.023 mol) in 25 % aqueous ammonia (20 mL) and THF (20 mL) was heated at 100C for 18 h in a steel bomb. The reaction was cooled to ambient temperature and the resulting crude material was evaporated to minimum. The residual material was triturated with water (15 mL), filtered and dried to afford 2-amino-3-chloropyrazine as a buff- coloured crystalline solid (2.75 g, 90%). MS (ES+) m/z: 130. 1H NMR (400 MHz, CDCl3): delta 7.94 (d, J=2.53 Hz, 1H), 7.72 (d, J=2.53 Hz, 1H), 4.90-5.12 (br. s, 2H).

The synthetic route of 4858-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Surase, Yogesh B.; Samby, Kirandeep; Amale, Sagar R.; Sood, Ruchi; Purnapatre, Kedar P.; Pareek, Pawan K.; Das, Biswajit; Nanda, Kamna; Kumar, Subodh; Verma, Ashwani K.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3454 – 3459;,
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. 912773-24-1, name is 6-Bromoimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., name: 6-Bromoimidazo[1,2-a]pyrazine

General procedure: To a solution of cycloalkenyl iodide (1.00 equiv) in Et 2 O (0.5 M) wasslowly added a solution of n-BuLi (2.44 M in hexane, 1.10 equiv) at-78 C. After stirring for 30 min at the aforementioned temperature, B(Oi-Pr)3 (1.15 equiv) and THF (total concn 0.25 M) were added andthe resulting mixture stirred for an additional 1 h at room tempera-ture. Pd(dppf)Cl2·CH2C2 (4 mol%), the cross-coupling partner (aromatic or vinylic iodide, bromide, tosylate or chloride) (0.90 equiv) andan aqueous solution of NaOH (1.5 equiv 1.00 M) were subsequentlyadded and the reaction mixture was stirred overnight. The crude ma-terial was extracted with Et2O (3 × 20 mL), washed with a saturated aqueous solution of sodium chloride (20 mL), dried over magnesiumsulfate, filtered, concentrated and purified via flash column chroma-tography.

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; Baumann, Andreas N.; Eisold, Michael; Music, Arif; Didier, Dorian; Synthesis; vol. 50; 16; (2018); p. 3149 – 3160;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

59489-71-3, name is 2-Amino-5-bromopyrazine, 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. SDS of cas: 59489-71-3

5-(thior)hen-3-yl)pvrazin-2-amine (N); In a dry 100 mL round bottom flask, a mixture of M (2.30 g, 13 mmol), thiopherie-3-boronic acid (2.54 g, 20.0 mmol), Pd(PPh3)4 (2.29 g, 2.0 mmol) and K2C03 (5.47 g, 40.0 mmol) in DMF (40 mL) was bubbled with N2 for 10 min, then the mixture was stirred at 100 C for 16 hours. The resulting mixture was evaporated to dryness. The residue was purified using column chromatography (silica gel, 2:1:7 hexane/CH2CI2/EtOAc). The fractions containing product were evaporated to dryness under vacuum to yield compound N as a light brown solid (1.63 g, 9.22 mmol, 71%). ¹H NMR (DMSO-d6, 300 MHz) No. 6.46 (bs, 2H), 7.55-7.65 (m, 2H), 7.85 (bs, 1 H), 7.90 (d, 1 H, J, 1.4), 8.42 (d, 1 H, J, 1.4).

The synthetic route of 59489-71-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, INC.; WO2005/113548; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 72788-94-4, name is 2-Chloro-5-(hydroxymethyl)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 72788-94-4, Computed Properties of C5H5ClN2O

(5-chloropyrazin-2-yl)methanol (780 mg, 5.40 mmol), ethyl 4-pyrazolecarboxylate(765 mg, 5.46 mmol) and potassium carbonate (283 mg, 2.05 mmol) andtriphenylphosphine (1.57 g, 6.01 mmol) are suspended in anhydrous tetrahydrofuran(20 mL) and cooled to 000. Diisopropyldicarboxylate (1.18 mL, 6.01 mmol) is added,the mixture allowed to warm to room temperature and stirred for three hours. The solvent is evaporated and the residue partitioned between dichloromethane and water and the phases separated. The organic extracts are washed with brine, dried over sodium sulfate and the solvent removed under vacuum. The residue is purifiedby flash chromatography (30-50% ethyl acetate in cyclohexane) to give the desired intermediate as an impure product (Yield 2.12 g).LC (Method 5): tR = 0.95 mm; Mass spectrum (ES+): mlz = 267 [M+H].

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FRATTINI, Sara; BAKKER, Remko; GIOVANNINI, Riccardo; FOSSATI, Giacomo; HAMPRECHT, Dieter; LINGARD, Iain; PAUTSCH, Alexander; WELLENZOHN, Bernd; (168 pag.)WO2017/72021; (2017); 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. 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 13924-95-3

To a solution of methyl 5-hydroxypyrazine-2-carboxylate (9.25 g, 60.0 mmol) in /V,/V-dimethylformamide (120 mL) were added potassium carbonate (24.8 g, 179 mmol) and sodium chloro(difluoro)acetate (18.3 g, 120 mmol). The mixture was heated to 100 C for 15 minutes, whereupon it was filtered, and the filter cake was washed with ethyl acetate (2 x 50 mL). The combined filtrates were poured into saturated aqueous ammonium chloride solution (200 mL) and extracted with ethyl acetate (3 x 200 mL); the combined organic layers were washed sequentially with saturated aqueous sodium bicarbonate solution (2 x 300 mL) and with saturated aqueous sodium chloride solution (2 x 300 mL), dried, filtered, and concentrated in vacuo. Chromatography on silica gel (Gradient: 0% to 15% ethyl acetate in petroleum ether) afforded the product as a yellow solid. Yield: 1 .7 g, 8.3 mmol, 14%. 1 H NMR (400 MHz, CDCI3) delta 8.92 (d, J=1 .2 Hz, 1 H), 8.47 (d, J=1 .2 Hz, 1 H), 7.49 (t, JHF=71 .3 HZ, 1 H), 4.04 (s, 3H).

According to the analysis of related databases, 13924-95-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; BECK, Elizabeth Mary; BUTLER, Christopher Ryan; ZHANG, Lei; O’NEILL, Brian Thomas; BARREIRO, Gabriela; LACHAPELLE, Erik Alphie; ROGERS, Bruce Nelsen; WO2015/155626; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, 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. category: Pyrazines

Step C: Preparation of (laS,5aS)-2-(Pyrazin-2-yl)-la,2,5,5a-tetrahydro-lH-2,3- diaza-cyclopropa[a]pentalene-4-carboxylic Acid Ethyl Ester. Method KKKTo a solution of (lS,5R)-bicyclo[3.1.0]hexan-2-one (52.9 g, 539 mmol) and diethyl oxalate (0.073 L, 539 mmol) in absolute ethanol (0.9 L) (not denatured with methanol) was added a THF solution of potassium tert-butoxide (1.0 M, 0.539 L, 539 mmol) over 15 min (maintaining the temperature below 43 C). The resulting yellow solution was stirred at 40 C for 3.5 h. 2-Hydrazinylpyrazine (59.4 g, 539 mmol) was added followed by a 6.0 M aqueous solution of hydrogen chloride (0.270 L, 1618 mmol). The reaction was stirred at 50 C for 1.5 h. The mixture was poured into ice -water (5 L). A precipitate appeared immediately. After sitting for 30 minutes in an ice bath, the solid was collected by filtration, rinsed with water (5 x 1 L), and dried to give the title compound (106 g) as an off-white solid .H NMR. LCMS m/z = 271.2 [M+H]+; lU NMR (400 MHz, CDC13) delta 0.47 (td, 7 = 4.7, 3.3 Hz, 1H), 1.27 (td, 7 = 8.0, 4.9 Hz, 1H), 1.41 (t, 7 = 7.1 Hz, 3H), 2.26-2.32 (m, 1H), 2.77-2.82 (m, 1H), 2.88 (dd, 7 = 16.7, 1.4 Hz, 1H), 2.99 (dd, 7 = 16.6, 6.4 Hz, 1H), 4.40 (q, 7 = 7.1 Hz, 2H), 8.41 (dd, 7 = 2.5, 1.5 Hz, 1H), 8.52 (d, 7 = 2.5 Hz, 1H), 9.40 (d, 7 = 1.5 Hz, 1H).

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

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; THATTE, Jayant; BLACKBURN, Anthony C.; HAN, Sangdon; JONES, Robert M.; JUNG, Jae-Kyu; MONTALBAN, Anthony Garrido; PAL, Biman B.; RUETER, Jaimie Karyn; STRAH-PLEYNET, Sonja; THORESEN, Lars; XIONG, Yifeng; YUE, Dawei; ZHU, Xiuwen; WO2012/116279; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 873-40-5,Some common heterocyclic compound, 873-40-5, name is 2,3,5-Trichloropyrazine, molecular formula is C4HCl3N2, 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, 3, 5-trichloropyrazine (70.50 g, 384.36 mmol, 1 equiv) and ammonia solution(25% wt, 364.00 g, 400 mL, 2.68 mol, 6.14 equiv) were added to a l-L sealed reactor. The mixture was heated to 80 C and stirred for 24 h, and the reaction was completed. The reaction mixture was cooled to 30 C and filtered to give a brown filter cake. The brown filter cake was dissolved in acetone(50 mL), and filtered. To the filtrate was added petroleum ether (300 mL). The suspension was stirred for 4 h, and filtered to give the crude product. The crude product was slurried in combined solvents of petroleum ether and acetone (10/1, 200 mL) and filtered to give the product Y7d (51.00 g, 307.91 mmol, 80% yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) d = 7.63 (s, 1H).

The synthetic route of 873-40-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FEI, Zhongbo; LU, Gang; WAN, Yinbo; WANG, Jianhua; WU, Quanbing; ZHANG, Hao; (116 pag.)WO2020/65453; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 (1.85 g, 10.28 mmol), (R)-piperidine-1,3-dicarboxylic acid 1-benzylester (2.71 g, 10.28 mmol) and HATU (4.1 g, 10.79 mmol) in dichloromethane (75 mL) was added triethylamine (5.73 mL, 41.1 mmol) and the reaction mixture was stirred at 0C for 4 hr. and after warming up to 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 to give 5.03 g of crude (R)-benzyl 3-((3-chloropyrazin-2-yl)methylcarbamoyl)piperidine-1-carboxylate (126%) which was used directly in the next step.

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

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

Related Products of 4430-75-5, These common heterocyclic compound, 4430-75-5, name is Octahydro-2H-pyrido[1,2-a]pyrazine, 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.

Step A Ethyl 3-(octahydro-2H-pyrido[1,2-a]pyrazin-2-yl)propionate A solution of 7 g of octahydro-2H-pyrido[1,2-a]pyrazine and 15 ml of ethyl acrylate in 100 ml of acetonitrile is refluxed for 24 hours and then concentrated to dryness in vacuo to yield the expected product.

The synthetic route of 4430-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Goldstein, Solo; Poissonnet, Guillaume; Parmentier, Jean-Gilles; Lestage, Pierre; Lockhart, Brian; US2003/195216; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem