Tag: M.W=100-200

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

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

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

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

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

Electric Literature of 6164-79-0, 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. 6164-79-0 name is Methyl 2-pyrazinecarboxylate, 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.

A solution of the product of Example 83A (6.91 g, 50 mmol) in THF (Aldrich, anhydrous, 150 mL) was cooled down to -78 C. and a solution of LiAlH4 (Aldrich, 1.898 g, 50.0 mmol) in THF (50 mL) was added slowly via an additional funnel. The mixture was stirred at -78 C. under N2 for 1 hour, and then it was then carefully and slowly quenched with HOAc (Aldrich, 10 mL) at -70 C. The mixture was slowly warmed up to ambient temperature and stirred for 10 hours. After being concentrated, the residue was stirred with HCl (2N, 15 mL) in CH2Cl2 (300 mL) for 20 minutes and then filtered through diatomaceous earth to remove solid inorganic salt. The organic filtrate solution was concentrated and the residue was dissolved in EtOAc (100 mL) and filtered through diatomaceous earth again. The organic filtrate solution was concentrated to give the titled compound. 1H NMR (300 MHz, DMSO-d6) delta 8.91 (dd, 1H), 8.94 (d, 1H), 9.12 (d, J=1.6 Hz, 1H), 10.08 (s, 1H) ppm; MS (DCI/NH3) m/z 109 (M+H)+.

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

Reference:
Patent; ABBOTT LABORATORIES; US2009/306096; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 914452-71-4,Some common heterocyclic compound, 914452-71-4, name is 2-Bromo-6-methylpyrazine, molecular formula is C5H5BrN2, 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 stirred solution of 2-bromo-6-methyl-pyrazine 51-3 (812 11 mg, 4.69 mmol) and methyl J – chloro-4-methyl-piperidine-4-carboxylate 51-2 (1000 mg, 5.16 mmol) in toluene (25 mL) was added cesium carbonate (4.59 g, 14.08 mmol). The reaction was degassed with argon for 10 minutes. Xanthphos (135 80 mg, 234.70 umoi) and Pd2(dba)3 (214 92 mg, 234.70 umoi) were added to the reaction mixture and the reaction mixture was heated at 90C for 16 hours. Reaction mixture was cooled to room temperature and diluted with ethyl acetate and water. Layers were separated and the organic layer was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified by combiflash chromatography (eluting at 2 % methanol in di chi or om ethane) to afford methyl 4-methyl- 1 -(6- methylpyrazin-2-yl)piperi dine-4-carboxyl ate 51-4 (630 mg, 2.53 mmol, 53.83% yield) as brown gum. LC MS: ES+ 250.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-6-methylpyrazine, its application will become more common.

Reference:
Patent; C4 THERAPEUTICS, INC.; VEITS, Gesine, Kerstin; HE, Minsheng; HENDERSON, James, A.; NASVESCHUK, Christopher, G.; PHILLIPS, Andrew, J.; GOOD, Andrew, Charles; (471 pag.)WO2019/191112; (2019); 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. 22047-25-2, name is Acetylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Safety of Acetylpyrazine

Preparation 21-Pyrazin-2-yl-ethylamineThe synthetic procedure used in this preparation is outlined below in Scheme C. To a solution of 1-pyrazin-2-yl-ethanone (2.0 g, 15.85 mmol) and ammonium acetate (19.337 g, 158.5 mmol) in methanol (50 mL) was added sodium cyanoborohydride (0.7 g, 11.1 mmol) in one portion. The reaction mixture was stirred overnight at room temperature. After removal of methanol, water (20 mL) was added to the residue and the resulting solution was basified by addition of sodium hydroxide to pH=13. The aqueous solution was extracted with dicholromethane and the combined organic phase was dried over sodium sulfate. Removal of the solvent under reduced pressure afforded 14.62 g of 1-pyrazin-2-yl-ethylamine, yield: 75%. MS (M+H)=124.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 22047-25-2.

Reference:
Patent; Chen, Li; Dillon, Michael Patrick; Feng, Lichun; Yang, Minmin; US2010/324069; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 23611-75-8, 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. 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 124 (1.5 g, 8.72 mmol) in NMP (10 vol) was added DIPEA (7.6 ml, 43.60 mmol) and /V-Boopiperazine (3.24 g, 17.44 mmol) at RT. The reaction mixture was stirred at 100 C for 16 h. The progress of the reaction was monitored by TLC. The reaction mixture was quenched with water and was extracted with ethyl acetate (3 x 100 ml). The combined organic layer was concentrated under reduced pressure to get the crude material. The crude compound was purified via column chromatography on silica-gel (100-200 mesh, 15-20 % EtOAc: Pet ether) to afford 125 (1 g, 35 %) as a colorless liquid. To a stirred solution of 125 (1 g, 3.10 mmol) in dry THF (10 mL) was added LiAIH4solution (2 in THF, 0.776 ml, 1.55 mmol) drop wise at -20 C and stirred at the same temperature for 2 h. The progress of the reaction was monitored by TLC. TLC showed formation of a polar spot with complete consumption of starting material. The reaction was quenched with saturated sodium sulphate and filtered the reaction mixture through a pad of celite. The filtrate was evaporated under reduced pressure to get the crude residue. The crude compound was purified via column chromatography on silica gel (100-200 mesh, 25 -28 % EtOAc: Pet ether) to afford 126 (500 mg, 54 %) as a pale yellow solid. To a stirred solution of 126 (500 mg, 1.70 mmol) in DC (10 vol) was added TEA (0.715 mL, 5.10 mmol) and methane sulfonyl chloride (0.197 mL, 2.55 mmol) drop wise at 0 C. The reaction mass was stirred at RT for 2 h. TLC showed formation of a non-polar spot with complete consumption of starting material. The reaction mixture was concentrated under reduced pressure to get 400 mg of crude 127 as a yellow syrup. The crude compound was as such used in the next step without any further purification. To a stirred solution of 6-103 (375.4 mg, 1.29 mmol) in D F (20 ml) was added K2C03(355.6 mg, 2.57 mmol) at RT and was stirred at RT for 10 min. Then 127 (400 mg, crude, 1 .075 mmol) in DMF was added drop wise at RT. The reaction mass was heated to 90 C for 16 h. The reaction mixture was quenched with ice cold water and was extracted into EtOAc (2 x 100 ml). The combined organic layers were washed with water, brine and dried over Na2S04.The solvent was removed under reduced pressure to get the crude material. The crude compound was purified by C-18 column with 0.01 % HCOOH in water and acetonitrile] and to afford 128 (95 mg, 10 %) as a white solid. To a stirred solution of 128 (90 mg, 0.158 mmol) in 1 ,4- dioxane (10 vol) was added 4 HCI-dioxane (10 mL) at 0 C. The reaction mixture was stirred at RT for 2 h. The solvent was removed under reduced pressure to get the residue, which was triturated with ether to get 85 mg of 6-205 as HCI salt.1H NMR (400 MHz, DMSO- d6): delta 9.14 (br s, 3H), 8.61 (br d, J = 7.8 Hz, 1 H), 8.36 (s, 1 H), 8.02 (s, 1 H), 7.40 – 7.31 (m, 1 H), 7.24 (d, J – 7.8 Hz, 1 H), 5.24 – 5.06 (m, 2H), 4.97 (s, 2H), 4.47 – 4.35 (m, 1 H), 3.90 – 3.76 (m, 4H), 3.17 (br s, 4H), 2.49 – 2.37 (m, 3H), 2.22 – 2.11 (m, 1 H), 0.97 (br d, J – 6.8 Hz, 6H). LC-MS: m/z 468.34 [M+H]+. HPLC purity: 95.10% (220 nm), 96.29% (254 nm) and chiral HPLC purity is 95.97% (247 nm).

The synthetic route of Methyl 6-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; CARTER, David Scott; HALLADAY, Jason S.; JACOBS, Robert T.; LIU, Yang; PLATTNER, Jacob J.; ZHANG, Yong-Kang; WITTY, Michael John; (149 pag.)WO2017/195069; (2017); 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. 59489-71-3, name is 2-Amino-5-bromopyrazine, A new synthetic method of this compound is introduced below., Safety of 2-Amino-5-bromopyrazine

19.1. 5-aminopyrazine-2-carbonitrile Heat a suspension of 1.85 g (20.7 mmol) of copper cyanide and 1 g (20.7 mmol) of sodium cyanide in 20 ml of DMF to 135 C., while stirring. Add 3.6 g (20.7 mmol) of 5-bromopyrazin-2-amine to the solution obtained, and maintain the temperature of 135 C. for 18 h. Then add 2 equivalents of sodium cyanide and of copper cyanide and continue heating for a further 24 h. After cooling, add 100 mL of 0.3N aqueous solution of sodium cyanide, stir the mixture for 1 h at 40 C., then distribute it in 300 mL of EtOAc/water 1:1 mixture. After washing with 2*100 mL of water, dry the organic phase over Na2SO4 and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluding with a cyclohexane/EtOAc gradient from 0 to 100% of EtOAc. After concentration under reduced pressure, we obtain 1.24 g of 5-aminopyrazine-2-carbonitrile in the form of oil. Yield=50%

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

Reference:
Patent; Sanofi Aventis; US2009/318473; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem