Tag: M.W=200-300

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. 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 330786-09-9

At 0 C. a solution of 12 (2.59 g) and NEt3 (1.744 ml) in DMF (20 ml), was added to a solution of 6 (2.95 g) in DMF (5 ml) and stirred for 16 h at 25 C. The mixture was diluted with ethyl acetate (70 ml) and washed with water (50 ml). The aqueous phase was extracted with ethyl acetate (30 ml), the combined organic phases washed with brine, dried over Na2SO4 and the solvent evaporated. Chromatography on silica (gradient cyclohexane/ethyl acetate) gave 13 (950 mg) as a yellow solid. UPLC/MS found for C17H25ClN4O4 as (M+1)+ 385.0, UPLC retention time 1.03 min.

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; NOVARTIS AG; Thoma, Gebhard; Smith, Alexander Baxter; van Eis, Maurice; US2013/310387; (2013); 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. 58139-03-0, name is 2-Iodo-6-methoxypyrazine, A new synthetic method of this compound is introduced below., Formula: C5H5IN2O

2. 3-[2-(6-Methoxypyrazin)yl]-1-azabicyclo[2.2.2]octan-3-ol t-Butyllithium (20 ml of a 1.7M solution in pentane, 35.3 mmol) was added dropwise to a rapidly stirred solution of 2-methoxy-6-iodopyrazine (4.17 g, 17.6 mmol) in ether (80 ml), at -40° C. After 0.25 h a solution of quinuclidinone (2.21 g, 17.6 mmol) in ether (60 ml) was added dropwise and the reaction mixture warmed to room temperature and stirred for 2 h. Water (35 ml) was added and extracted with ethylacetate (4*100 ml). The combined extracts were dried (Na2 SO4), the solvent removed under vacuum and, the residue chromatographed through alumina, eluding with dichloromethane/methanol (93:7) to give 3-[2-(6-methoxypyrazin)yl]-1-azabicyclo [2.2.2]octan-3-ol (1.65 g); delta (360 MHz, CDCl3) 1.37-1.51 (3H,m, –CH2 and CH of CH2); 1.70-1.90(1H, brs, OH); 1.94-1.96-(1H,m,CH); 2.20-2.32(1H,m,CH of CH2); 2.80-3.10(5H,m,2*CH2 and CH of CH2) 3.74(1H,dd, J=2 and 14.6 Hz, CH of CH2); 3.99(3H,s,Me); 8.15(1H,s,pyrazine-H); 8.39(1H,s,pyrazine-H).

The synthetic route of 58139-03-0 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

Adding a certain compound to certain chemical reactions, such as: 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-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 6966-01-4, Application In Synthesis of Methyl 3-amino-6-bromopyrazine-2-carboxylate

Palladium acetate (0.145 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium complex with DCM (0.702 g) were dissolved in DMF (65 ml) and heated to 50 C for 15 minutes. After cooling to room temperature 3-amino-6-bromo-pyrazine-2-carboxylic acid methyl ester (5.0 g), 4-fluoro-phenyl boronic acid (3.82 g) and triethylamine (4.5 ml ) were added and the mixture heated to 90 C for 20 hours with stirring. The solvent was evaporated and the residue dissolved in DCM. The organic phase was washed with dilute ammonium hydroxide solution and water. After drying with sodium sulphate and filtration the solvent was evaporated and the residue purified by column chromatography on silica gel eluting with hexane: ethyl acetate, 3: 1 to give 3-amino-6-(4-fluorophenyl)-pyrazine-2- carboxylic acid methyl ester (0.670 g). ‘H NMR (CDCI3) 8 ppm: 3.92 (s, 3H), 6.4 (bs,1H), 7.1 (m, 2H), 7.8 (m, 2H), 8.5 (s,1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-6-bromopyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2005/123733; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 17890-77-6, These common heterocyclic compound, 17890-77-6, name is 3-Amino-6-bromopyrazine-2-carboxamide, 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.

In the equipped with magnetic stirring, of the reflux condensation tube (with drying tail pipe) of 250 ml in three-necked bottle, adding 13.1g (about 0.06 muM) 3 – amino pyrazine -2 – formamide, 60 ml of acetic anhydride, 60 ml ethyl trimethyl orthoformate, stirring under heating to reflux 4h, started when the reflux temperature 136 C, gradually reduced to 95 C, cooling to room temperature, filter, ice laundering, a brown solid.The crude isopropyl alcohol and water (1:1) about 300 ml of mixed the fluid is heavy crystallization, heating completely dissolved, add 2g activated carbon to decolorize 30min, heat filtering, washing. Cooling separating white solid. 60 C drying. Be 11.24g white powder that is 6 – bromo -4 (3H) dihydropteridinones. Yield: 82.5

The synthetic route of 17890-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Li Zhulai; (15 pag.)CN106699759; (2017); A;,
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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-amino-6-bromopyrazine-2-carboxylate

Triisopropyl borate (2.7 mL, 11.6 mmol) was added to a solution of 1- [ (4- bromophenyl) SULFONYL]-4-METHYLPIPERAZINE in (1.24 g, 3.87 mmol; described: in Keasling, H. H. et el. J. Med. Chem. 1965, 8, 548-550) in anhydrous tetrahydrofuran (25 mL) at-78 C under an atmosphere of nitrogen, followed by dropwise addition of n-butyllithium (9.8 mL, 15.5 mmol). The resulting mixture was stirred at-78 C for 30 min, then allowed to warm to room temperature. HCl (3 M aq, 7.8 mL, 23.2 mmol) was added and the mixture was stirred at room temperature for 10 min. Sodium carbonate (4.1 g, 38.7 mmol) was added followed by the addition of methyl 3-amino-6-bromo-2-pyrazinecarboxylate (0.79 g, 3.4 mmol; described in: H. Ellingson, J. Amer. Chem. Soc. 1949,2798) and Pd (dppf) Cl2 (95 mg, 0.12 mmol). The resulting mixture was heated at 55 C overnight. Silica was added, the solvent was evaporated and the crude mixture was purified by column chromatography on silica using CHLOROFORM/METHANOL, (99: 1), as the eluent to give 0.923 g (69% yield) of the base as a yellow solid : 1HNMR (DMSO-D6) S 9.0 (s, 1 H), 8.22 (d, J = 7 Hz, 2 H), 7.80 (d, J = 7 HZ, 2 H), 7.62 (BR S, 2 H), 3.90 (s, 3 H) 2.91 (m, 4 H), 2.36 (m, 4 H), 2.12 (s, 3 H); 13CNMR (DMSO-D6) 8 166. 2,155. 1,145. 8,140. 33,127. 5,134. 0,128. 1, 125.7, 109.1, 53.5, 52.3, 45.7, 45.2 ; MS (ESP) M/Z 392 (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

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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H2BrIN2

Description 66: 2-bromo-5-(trifluoromethyl)pyrazine (D66); Potassium fluoride (238 mg, 4.09 mmol) and copper(I) iodide (779 mg, 4.09 mmol) were mixed and heated under vacuum using heat gun (temperature 360 0C, on display of heating gun) for 20 minutes (until a greenish colour of the mixture appeared). After cooling at room temperature, DMF (4 ml) and NMP (4.00 ml) were added followed by (trifluoromethyl)trimethylsilane (0.603 ml, 3.77 mmol) and 2-bromo-5-iodopyrazine D65 (896 mg). The resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was poured in 200 ml of 6N NH3 water solution and was extracted twice with Et2O(3 x 50 ml). Gathered Et2O layers were dried over Na2SO4.Diethyl ether was distilled by Claisen apparatus. It was recovered the title compound D66(586 mg).1H NMR (400 MHz, CHLOROFORM- d) delta ppm 8.73 – 8.81 (m, 1 H) 8.84 (s, 1 H)

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; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); 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 117719-17-2 as follows. Formula: C8H11BrN4O

Preparation of Intermediate I-57. A mixture of Intermediate I-02 (8.17 g, 31.52 mmol) and 1,3-dichloroacetone (6.0 g, 47.29 mmol) in 2-propanol (15 mL) was heated in a sealed tube at 55 C. for 2 days. On cooling, the mixture was filtered and rinsed with Et2O and MeOH. The solid was purified by flash chromatography on silica gel (MeOH:DCM, 5:95) and the product obtained was washed with MeOH and dried to give Intermediate I-57 (3.97 g, 38%).

According to the analysis of related databases, 117719-17-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Centro Nacional De Investigaciones Oncologicas (CNIO); US2012/83492; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 330786-09-9,Some common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, molecular formula is C6H4Cl2N2O2, 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 solution of methyl 3,5-dichloropyrazine-2-carboxylate (0.312 g, 1.51 mmol) in THF (4.5 mL) at RT was added sodium hydride (60% wt. dispersion, 0.199 g, 4.98 mmol) and methanol (0.200 mL, 4.94 mmol). The reaction mixture was stirred at RT for 30 min, diluted with EtOAc, and quenched with saturated NH4C1. The reaction mixture was partitioned between brine and EtOAc. The aqueous phase was extracted with EtOAc (3 x) and the combined organic extracts were washed with brine (1 x), dried over MgS04, filtered, and concentrated. Purification by flash column chromatography on silica gel (10% to 50% EtOAc in hexanes) gave ethyl 3,5-dimethoxypyrazine-2-carboxylate (0.314 g, 1.48 mmol, 98% yield) as an off white solid. LC/MS (ESf ) m/z = 199.1 (M+H)+

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

Reference:
Patent; AMGEN INC.; MINATTI, Ana Elena; LOW, Jonathan, D.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BROWN, James; FROHN, Michael, J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul, E.; LOPEZ, Patricia; MA, Vu Van; NISHIMURA, Nobuko; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert, M.; SHAM, Kelvin; SMITH, Adrian, L.; WHITE, Ryan; XUE, Qiufen; WO2014/138484; (2014); 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. 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3,5-Dibromo-1-methylpyrazin-2(1H)-one

A mixture of 3,5-dibromo-l-methyl-2(lH)pyrazinone (2.0g;7.5mmol), 2-(4-Amino-phenyl)-ethanol (1.Og; 7.3mmol), and l-methyl-2- pyrrolidinone (ImL) was heated at 120 0C for lhr. The mixture was cooled to room temperature, diluted with dichloromethane and filtered to give a dull brown oil. This was dissolved in CH2Cl2 and washed with 0.0 IN NaOH, and dried over solid sodium sulfate. After filtration and evaporation of the CH2Cl2 layer, the resulting brown solid was chromatographed on silica using methanol/CH2Cl2 (1:9) as eluent to provide 2.0g of 5-bromo-3-[4-(2-hydroxy-ethyl)-phenylamino]-l-methyl-lH-pyrazin-2-one (1) as a light tan solid. MS 324.23 (M+H).

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 87486-34-8.

Reference:
Patent; CGI PHARMACEUTICALS, INC.; WHITNEY, James A.; DI PAOLO, Julie; VALLECA, Mark A.; BRITELLI, David R.; CURRIE, Kevin S.; DARROW, James W.; KROPF, Jeffrey E.; LEE, Tony; GALLION, Steven L.; MITCHELL, Scott A.; PIPPEN, Douglas A.I.; BLOMGREN, Peter A.; STAFFORD, Douglas Gregory; WO2008/33858; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 117719-17-2, 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. 117719-17-2 name is 5-Bromo-3-morpholinopyrazin-2-amine, 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 5-bromo-3-morpholinopyrazin-2-amine (0.200 g, 0.772 mmol) in DME (1.5 mL), 2-chlorocyclopentanone (0.1 6 mL, 1.158 mmol) was added. The mixture was heated at 120 C for 16 h, until the reactants were consumed as determined by LCMS analysis. The reaction mixtures were diluted with DCM (100 ml_) mixed, washed with saturated aqueous solution of NaHC03, brine, dried over Na2S04 and concentrated in vacuo. The dark residue was purified by biotage (cyclohex/EtOAc 1 :1) to obtain 30 mg of desired compound I-04 as a white solid, which was used in next reaction step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-3-morpholinopyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONC&Oacgr;LOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ ARISTEGUI, Sonsoles; GONZALES CANTALAPIEDRA, Esther; HERNANDEZ HIGUERAS, Ana Isabel; VARELA BUSTO, Carmen; WO2011/36461; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem