Month: June 2021

Related Products of 4774-14-5, 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. 4774-14-5, name is 2,6-Dichloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of tert-butyl azetidin-3-ylcarbamate hydrochloride (LXII) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture was added 2,6-dichloropyrazine (LXIII) (1.428 g, 9.58 mmol) and the reaction was stirred at 95C for 3 h. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous Na2504, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes-*hexanes:EtOAc 1:1) to yield tert-butyl (1- (6-chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXIV) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C12H17C1N402 mlz 285.1 (M+H).

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

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (307 pag.)WO2017/23989; (2017); 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 297172-19-1 as follows. Formula: C6H9N3

A flask was charged with tert-butyl (R)-3-((2-(N,N-bis(4- methoxybenzyl)sulfamoyl)-4-iodo-3-(1-(4-methoxybenzyl)-1H-tetrazol-5- yl)phenyl)sulfonamido)pyrrolidine-1-carboxylate and tert-butyl (R)-3-((2-(N,N-bis(4- methoxybenzyl)sulfamoyl)-4-iodo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5- yl)phenyl)sulfonamido)pyrrolidine-1-carboxylate (REFERENCE EXAMPLE 5) (0.15 g, 0.156 mmol), 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine (0.038 g, 0.313 mmol), Cs2CO3 (0.153 g, 0.469 mmol) and Pd(dppf)Cl2 (0.023 g, 0.031 mmol). The vial was sealed, degassed with N2, and filled with DME (1.56 mL). The resulting mixture was heated overnight at 80 C. The reaction mixture was filtered through diatomaceous earth. The filtrate was concentrated and the residue purified by silica gel column chromatography using (gradient 0-10%) MeOH in DCM as the mobile phase to afford the title compound. LC/MS [M+H]+: 955.82.

According to the analysis of related databases, 297172-19-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DONG, Shuzhi; SCOTT, Jack, D.; TANG, Haiqun; ZHAO, Zhiqiang; YANG, Dexi; XIAO, Li; GU, Xin; JIANG, Jinlong; (85 pag.)WO2019/135920; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 56423-63-3, These common heterocyclic compound, 56423-63-3, name is 2-Bromopyrazine, 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.

To a reaction flask were added compound 16 (200 mg, 0.372 mmol), 2-bromopyrazine (50 mg, 0.27 mmol),Pd(dppf)Cl2 (10 mg, 0.01 mmol) and sodium carbonate (60 mg, 0.558 mmol), 5 mL glycol dimethyl ether and 0.9 mLwater were added, bubbled with nitrogen gas for 10 minutes, and the reaction was heated to 100 C in microwave andreacted for half an hour. After TLC detected the reaction was complete, the reaction was concentrated, purified by silicagel column chromatography to afford 35 mg of a product, yield: 20.3%. LC-MS(APCI): m/z = 464.5 (M+1)+. 1H NMR(400 MHz, CDCl3) delta 8.78 (d, J = 2.0 Hz, 1H), 8.73 (s, 1H), 8.64 (s, 1H), 8.54 (d, J = 2.1 Hz, 1H), 8.11 (d, J = 2.0 Hz,1H), 7.95 (s, 1H), 7.67 (d, J = 8.9 Hz, 2H), 7.23 (d, J = 8.6 Hz, 2H), 5.28 (s, 1H), 5.14 (s, 1H), 3.70 – 3.57 (m, 1H), 3.52(d, J = 10.8 Hz, 1H), 3.42 (t, J = 11.6 Hz, 1H), 3.30 (t, J = 9.5 Hz, 1H), 2.26 – 2.17 (m, 1H), 2.02 (dd, J = 9.5, 3.8 Hz, 1H).

Statistics shows that 2-Bromopyrazine is playing an increasingly important role. we look forward to future research findings about 56423-63-3.

Reference:
Patent; Shenzhen Targetrx, Inc.; WANG, Yihan; ZHAO, Jiuyang; AL, Yixin; (55 pag.)EP3553056; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 957230-70-5, name is 3,6-Dibromopyrazin-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 957230-70-5, Recommanded Product: 3,6-Dibromopyrazin-2-amine

Synthesis of compound D as desc?bed in the general reaction scheme; 5,8-DiotabromoiotamiotadazofJ ,2- ajpyrazine.[00250] Bromoacetaldehyde diethyl acetal (49mL, 326mmol) and 48% hydrobromic acid is heated to reflux for 1 5h, then poured into propan-2-ol (60OmL) and quenched with NaHCO3. After filtering, 2,5-dibromo-3-aminopyrazme (41.34g, 163mmol) is added to the solution and heated at reflux overnight. The reaction is cooled and solvents removed in vacuo, followed by addition of aq NaHCO3 and extraction with EtOAc. The organic phase is dried over MgSO4, filtered, and concentrated in vacuo to afford a brown solid. 1H NMR (250MHz, CDCl3) delta(ppm)7.86 (IH, s), 7 93-7.94 (IH, d), 7.98-7.99 (IH, d), m/z (APCI) 278 (M+H)+; m.p 132-135C

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, 3,6-Dibromopyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 36070-80-1, 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. 36070-80-1 name is 5-Chloropyrazine-2-carboxylic acid, 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 RBF was charged with 3-pentyn-2-ol (2.06 mL, 22.08 mmol) and DMF (10 mL). Potassium t-butoxide, sublimed, 99.99% trace metals basis (1.24 g, 11.04 mmol) was added portionwise (cooling with water). The mixture was stirred at room temperature for 10 min until all t-BuOK went into solution, then 5-chloropyrazine-2-carboxylic acid (0.500 g, 3.15 mmol) was added in portions and the resulting brown suspension was heated at 75 C. for 45 minutes. The mixture was cooled to RT and diluted with water (20 ml) until all solids dissolved, then acidified with 2M HCl (5.5 ml) to pH 2. The resulting solution was extracted with EtOAc and the organic layer was washed with water and brine, filtered through a pad of celite and concentrated in vacuo. The resulting suspension was diluted with 3 mL heptane/EtOAc (20:1) mixture then filtered. The solid was washed with heptane and dried in vacuo to afford 5-(pent-3-yn-2-yloxy)pyrazine-2-carboxylic acid (424 mg, 2.056 mmol, 65.2% yield) as a tan solid. m/z (ESI) 207.1 (M+H)+.

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

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6705-33-5,Some common heterocyclic compound, 6705-33-5, name is Pyrazin-2-ylmethanol, molecular formula is C5H6N2O, 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.

Dissolve 2-pyrazinylmethanol (2.0 g, 18.1 mmol) in DCM (200 mL) and cool to 0C while stirring under nitrogen. Add thionyl chloride (4.63 mL, 63.6 mmol) drop wiseover 10 mm, and allow to warm to 25 C. Stir at room temperature for 16 h. Concentrate the mixture and then dilute with DCM. Wash the crude solution with saturated NaHCO3, dry over Mg504, filter, and concentrate. Dissolve the crude residue in DCM and purify by silica gel flash chromatography (hexane/EtOAc, 95:5 to 100% EtOAc gradient) to give the title compound as a pale yellow oil. 1H NMR (400 MHz, CDC13) oe 4.67 (s = 2H),8.50-8.55 (m, 2H), 8.73 (s, 1H).

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

Reference:
Patent; ELI LILLY AND COMPANY; CHEDID, Marcio; EISSA, Hisham Omer; ENGLER, Thomas Albert; FURNESS, Kelly Wayne; RANK, Kenneth B.; WOODS, Timothy Andrew; WROBLESKI, Aaron D.; WO2015/69512; (2015); 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. 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Chloro-3-hydrazinylpyrazine

To a 0 0C solution of 2-(4-chlorophenyl)-2-methylpropanoic acid (99.3 mg, 0.50 mmol) in THF (2 mL) was added 4-methylmorpholine (60.5 muL, 0.55 mmol). After 10 minutes, isobutyl chloroformate (67.4 muL, 0.52 mmol) was added dropwise over 2 minutes. After 2.5 h, a solution of Compound IA (72.3mg, 0.50 mmol) in THF (3 mL) was added dropwise over 2 minutes. After 10 minutes the cooling bath was removed and the reaction mixture was warmed to room temperature. After 3 h at room temperature, water (5 mL) and ethyl acetate (10 mL) were added, and the resulting mixture was stirred for 10 minutes. At the conclusion of this period, the organic phase was separated, dried over Na2SO4, and then concentrated in vacuo to yield a residue. The residue was purified by flash chromatography (SiC^ , 0-100% ethyl acetate / hexanes) to provide compound IB, which was used directly in the preparation of compound 1C set forth below. LC/MS (m/z) = 325 (M+H)+.

According to the analysis of related databases, 63286-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/130951; (2008); 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 622392-04-5 as follows. Safety of 2-Bromo-5-iodopyrazine

(1-((1-(trifluoromethyl)cyclobutyl)methyl)piperidin-4-yl)methanol (880 mg, 3.50 mmol) was dissolved in THF (30 mL). At 0 C., NaH (126 mg, 5.25 mmol) was added thereto, and stirred for 30 minutes. 2-bromo-5-iodopyrazine (1.09 g, 3.85 mmol) was added thereto, following with stirring at 55 C. for 10 hours. The reaction mixture was added with water, and extracted with EtOAc. The obtained organic layer was washed with saturated aqueous brine solution, dried over anhydrous MgSO4, and filtered. The filtrate was concentrated under reduced pressure. The obtained material was used without further purifying process

According to the analysis of related databases, 622392-04-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; Lee, ChangSik; Jang, TaegSu; Choi, DaeKyu; Ko, MooSung; Kim, DoHoon; Kim, SoYoung; Min, JaeKi; Kim, WooSik; Lim, YoungTae; US2015/166480; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 27398-39-6, 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. 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Step 1 To a solution of 3-chloropyrazine-2-carboxylic acid (2.0 g, 12.70 mmol, 1.0 eq.) and TEA (3.50 mL, 25.40 mmol, 2.0 eq.) in THF (50 mL) was added methyl chloroformate (1.2 mL, 15.20 mmol, 1.2 eq.) at 0° C. The mixture was stirred at 0° C. for 10 min and filtered. To this filtrate was added a suspension of NaBH4 (0.97 g, 25.40 mmol, 2 eq.) in water (1.0 mL) at 0° C. The mixture was stirred at 0° C. for 1 h, quenched with NH4Cl(aq) solution, and extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-chloropyrazin-2-yl)methanol (400 mg, 22percent) as a white solid. 1H NMR (400 MHz, MeOD) delta 8.58 (d, J=2.5 Hz, 1H), 8.38 (d, J=2.5 Hz, 1H), 4.84 (s, 2H). LRMS (M+H+) m/z 145.1.

The chemical industry reduces the impact on the environment during synthesis 3-Chloropyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Global Blood Therapeutics, Inc.; The Regents of the University of Califorina; Cytokinetics, Inc.; Metcalf, Brian; Chuang, Chihyuan; Warrington, Jeffrey; Paulvannan, Kumar; Jacobson, Matthew P.; Hua, Lan; Morgan, Bradley; US2015/344483; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 16298-03-6, 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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Preparation of 3-aminopyrazine-2-carbaldehyde EPO Mthetathyl-3-aminopyrazine-2-carboxylate (11g) was dissolved in THF and cooled to – 780C. Diisobutylaluminum hydride (1 M in hexanes, 25OmL) was added, and the reaction stirred at -78C for 4 hours. The reaction was then warmed to 00C for one hour before being quenched slowly by addition of 1 M hydrochloric acid. Ethyl acetate was added and the layers separated. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was triturated in hexanes to afford title compound (3.Og, 34%).1H NMR (400 MHz, DMSO-D6) delta ppm 7.73 (br, 2H), 8.07 (d, J=2.25 Hz, 1 H), 8.36 (d, J=2.11 Hz, 1 H), 9.95 (s, 1 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, Methyl 2-aminopyrazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/63167; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem