Category: Pyrazines

Application of 27825-21-4, 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. 27825-21-4, name is Methyl 3-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A solution of methyl 3-chloropyrazine-2-carboxylate (200.0 mg, 1.15 mmol, CAS 27825-21-4), (i?)-/V-[(3ri)-l,3-dihydrospiro[indene-2,4′-piperidin]-3-yl]-2-methylpropane-2- sulfmamide (772.0 mg, 1.26 mmol, 50% purity) and CsF (522.0 mg, 3.44 mmol) in DMSO (15.0 mL) was stirred at 60 C for 1 hour. The reaction mixture was poured into H20 (60.0 mL) and extracted with EtOAc (60.0 mL x 2). The combined organic layers were washed with brine (40.0 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give an orange residue. The residue was purified by flash silica gel chromatography (12 g column, ethyl acetate in petroleum ether from 0% to 65%) to give methyl 3-[(3ri)-3-{[(i?)-2-methylpropane-2-sulfmyl]amino}-l,3-dihydrospiro[indene-2,4′- piperidin]-l’-yl]pyrazine-2-carboxylate (450.0 mg, 89% yield) as a yellow oil. LCMS m/z [M+H]+= 443.1.

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

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); 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 1422772-78-8 as follows. HPLC of Formula: C7H4BrN3O2

Ice bath,(COCl) 2 (7.5 mL) and DMF (0.4 mL)Was slowly added dropwise to a solution of 2-bromo-5H-pyrrolo [2,3-b] pyrazine-7-carboxylic acid (60%, 4.00 g, 8.26 mmol) in dichloromethane (150 mL)Reaction at room temperature for 2 h. Concentrated under reduced pressure,The residue was dissolved in dichloromethane (120 mL)Cyclobutylamine (2.2 mL, 26 mmol) and triethylamine were added(2.4 mL) was added and the reaction was carried out overnight. The reaction was quenched with water (150 mL)Dichloromethane (150 mL x 3), and the organic layer was dried over anhydrous Na2SO4, (Eluent: Cl2CH2 / MeOH (v / v) = 30/1) to give 1.20 g of a tan solid Rate: 49.0%.

According to the analysis of related databases, 1422772-78-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd; Liu, Bing; Huang, Jiuzhong; Zhang, Yingjun; Xue, Yaping; Xing, Wei; Xu, Juan; Wu, Zuping; Yu, Tianxi; (106 pag.)CN106432246; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 6966-01-4, A common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, 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.

4- (PYRROLIDIN-1-YLSULFONYL) phenylboronic acid (0.33 g, 1.29 mmol), methyl 3-AMINO-6- bromopyrazine-2-carboxylate (0.25 g, 1.08 mmol; described in: H. Ellingson, J. Amer. CLIENT. Soc. 1949, 2798), K3PO3 (3 M, 1.1 ML, 3.2 mmol), and Pd (dppf) C12 (0.044 g, 54 , UMOL) were suspended in ethylene glycol dimethyl ether/water (1.5 : 0.5 mL) and heated in a microwave oven at 160 C for 10 min. The reaction was repeated 3 times. The combined product mixtures were evaporated with silica gel and the crude product was purified by chromatography on silica gel using a heptane to ethyl acetate gradient to give 0.96 g (82% yield) of the title compound: MS (ES) NAL, Z 363 (M++1).

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:
Patent; ASTRAZENECA AB; WO2004/55006; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

58138-79-7, name is 2,6-Diiodopyrazine, 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. HPLC of Formula: C4H2I2N2

1. 2-Iodo-6-allyloxypyrazine This was prepared from 2,6-diiodopyrazine (5.5 g, 16.6 mmol) and allyl alcohol by the procedure described for Example 31 part 1. Chromatography through silica gel using dichloromethane as eluant gave the pure product (2 g), delta (250 MHz, CDCl3) 4.83-4.86 (2H, m, CH2 O); 5.29-5.35 (1H, m, cis-vinyl-H); 5.39-5.48 (1H, m, trans-vinyl-H); 5.98-6.13 (1H, m, vinyl-H); 8.16 (1H, s, pyrazine-H); 8.40 (1H, s, pyrazine-H).

The synthetic route of 58138-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Limited; US5260293; (1993); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 312736-50-8, name is 3,5-Dichloropyrazine-2-carboxamide belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 3,5-Dichloropyrazine-2-carboxamide

107261 To a solution of 3,5-dichloropyrazine-2-carboxamide (Example 12, Step 2, 52 g, 0.27 mol) in acetonitrile (1 L) was added POC13 (146 g, 89 mL, 0.95 mol) at room temperature. The mixture was heated to 90-100 C for 4 h. The mixture was cooled to room tempetature and poured slowlyinto a vigorously stirring solution of saturated aq. NaHCO3. Evolution of gas was observed. The mixture was extracted with EtOAc (3 x). The combined organic layers were dried over sodium sulfate then concentrated under reduced pressure to give a residue. The residue was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound as a pale yellow solid. ?H NIVIR (400 MHz, CDC13): ppm 8.64 (s, 1H): ?3C NMR (101 IVIFIz, CDC13) ppm 150.8,150.43, 143.24, 128.06, 113.06.

The synthetic route of 312736-50-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FLX BIO, INC.; BECK, Hilary, Plake; BIANNIC, Berenger; BUI, Minna Hue, Thanh; HU, Dennis, X.; KETCHAM, John, Michael; POWERS, Jay, Patrick; REILLY, Maureen, Kay; ROBLES-RESENDIZ, Omar; SHUNATONA, Hunter, Paul; WALKER, James, Ross; WUSTROW, David, Juergen; YOUNAI, Ashkaan; ZIBINSKY, Mikhail; (396 pag.)WO2018/22992; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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 24241-18-7, COA of Formula: C4H3Br2N3

To a solution of 3,5-dibromopyrazin-2-amine (2.00 g, 7.91 mmol) in THF (24 mL)were added triethylamine (3.3 mL, 24 mmol), cuprous iodide (151 mg, 0.79 mmol) andPd(PPh3hCh (561 mg, 0.79 mmol). The mixture was cooled to -5 oc under nitrogen protection,then trimethylsilylacetylene (1.07 mL, 7.50 mmol) was dropwised slowly into the mixture. Afterthe addition, the mixture was warmed to 0 oc and stirred for 1.5 h. The mixture was concentratedin vacuo to remove the solvent and the residue was purified by silica gel column chromatography(PE/EtOAc (v/v) = 511) to give the title compound as black oil (42 mg, 94 %).MS (ESI, pos. ion) m/z: 272.00 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 8.04 (s, lH), 5.14 (s, 2H), 0.30 (s, 9H).

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-Amino-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (303 pag.)WO2018/108125; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

51171-02-9, name is Methyl 3-Bromo-2-pyrazinecarboxylate, 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. Computed Properties of C6H5BrN2O2

(B) Methyl 2-phenylamino-3-pyrazine carboxylate: A mixture of 9.5 g. of methyl 2-bromo-3-pyrazine carboxylate, 8.2 g. of aniline, 0.5 g. of p-toluene sulfonic acid and 100 ml. of water was stirred and refluxed for two hours. The reaction mixture was poured on ice, extracted with ethyl acetate, the organic extracts were dried and concentrated to yield an oil. The crude residue was eluted on a silica gel column with ethyl acetate-hexane (1:2) yielding the product of this example as a yellow solid, m.p. 72-75 C.

The synthetic route of 51171-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US4680297; (1987); A;; ; Patent; Schering Corporation; US4680298; (1987); A;; ; Patent; Schering Corporation; US4740511; (1988); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, 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. Safety of (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

General procedure: Butyl lithium (1.6 N solution in hexane, 1.05 equiv) was added to a solution of (2R)-1 (1 equiv) in anhydrous THF (5 mL) cooled to ?78°C, and the mixture was stirred for 45 min. Imine 2a?f (1 equiv) in THF (4 mL) was added, and the mixture was stirred at ?78°C for 8h. The reaction mixture was allowed to warm to ?10 °C, after which a pH=7 phosphate buffer solution (10 mL) was added, and the mixture was extracted with ethyl acetate (3×10 mL). The organic phase was separated and dried with Na2SO4, and the solvent was evaporated in vacuo. Compounds 3, 4 were purified by means of flash chromatography (SiO2, CH2Cl2/hexane=40/60 for 3a (Rf 0.2) and 4a (Rf 0.4); CH2Cl2/ethyl acetate=95/5 for 3d (Rf 0.4) and 4d (Rf 0.5), 3e (Rf 0.5) and 4e (Rf 0.6); CH2Cl2/ethyl acetate=98/2 for 4f (Rf 0.6)).

The synthetic route of (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cremonesi, Giuseppe; Dalla Croce, Piero; Gallanti, Maddalena; La Rosa, Concetta; Tetrahedron; vol. 70; 11; (2014); p. 2054 – 2058;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 63286-28-2,Some common heterocyclic compound, 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, molecular formula is C4H5ClN4, 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 3: 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine A mixture of 1-(3-chloropyrazin-2-yl)hydrazine (0.90 g, 62 mmol), triethyl orthoformate (2.3 mL), 14 mmol), and dry xylene (15 mL) was refluxed with stirring for 2 h. The mixture was brought to RT, diethyl ether was added and the suspension was filtered. The solid collected was washed with diethyl ether to afford 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine (0.60 g, 62% yield). MS m/z: 155.0 (M+1).

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

Reference:
Patent; Amgen Inc.; US2010/120774; (2010); 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. 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H8ClF3N4

Into a 50 mL round-bottom flask was added 20 mL dichloromethane, followed by the addition of phenyl-butyric acid derivative (3.73 g, 0.01 mol) and triazolopyrazine hydrochloride (228 g, 0.01 mol). The temperature of the reaction mixture was cooled down to 0 C. in an ice-salt bath. 1-Hydroxylbenzotriazole (1.62 g, 0.012 mol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.29 g, 0.012 mol) were further added. 3 g Triethylamine was then added dropwise and the mixture was stirred at room temperature for 24 h. The reaction solution was washed with 3×20 mL distilled water. The obtained organic layers were collected and dried over anhydrous magnesium sulfate for 1 h. Then, the desiccant was filtered off and the resulting reactant was concentrated to 4.64 g. The yield was 85%.

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 762240-92-6.

Reference:
Patent; ZHEJIANG HISOAR PHARMACEUTICAL CO., LTD.; Pan, Xianhua; Li, Weijin; Zhang, Qunhui; Ruan, Libo; Yu, Wansheng; Deng, Fei; Ma, Tianhua; Huang, Mingwang; He, Minhuan; US2013/281695; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem