Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-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 1458-18-0, Safety of Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

Preparative Example 72. Preparation of Table 1 Compound No. 207; A suspension of 100 (3.6 g, 16 mmol, Aldrich) and sodium hydroxide (1.6 g, 39 mmol) in water (30 ml_) was heated at reflux for 15 min. The solution was filtered, allowed to cool to room temperature, and was acidified with 1 N hydrochloric acid. The precipitated solid 101 (1.2 g, 36% yield) was collected by filtration, air-dried, and dried further under vacuum.

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; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/88920; (2006); 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 1082843-72-8 as follows. Quality Control of 6-Bromo-3-chloropyrazin-2-amine

General procedure: Sodium ethanethiolate (1.85 g, 21.95 mmol) was added to a solution of 4,6-dichloropyrimidin-5-amine (3.00 g, 18.29mmol) in methanol(100 mL) and heated at reflux for 3 hours. The reactionmixture was evaporated to dryness and redissolved in EtOAc (50 mL) and washed sequentially with water (50 mL) and saturated brine (50 mL). The organic phase was dried over MgSO4, filtered and evaporated toafford the crudeproduct. The crude product was purified by flash silica chromatography, elutiongradient 5% to 25% EtOAc in heptane. Pure fractions were evaporated to drynessto afford 4-chloro-6-(ethylthio)pyrimidin-5-amine (2.70 g, 78%) as a white solid;

According to the analysis of related databases, 1082843-72-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Boyd, Scott; Davies, Robert D.M.; Degorce, Sebastien L.; Groombridge, Sam; S. Scott, James; Stokes, Stephen; Tetrahedron Letters; vol. 57; 1; (2016); p. 152 – 154;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, 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

2-Bromo-5-iodopyrazine [CAS RN: 622392-04-5] (3.50 g, 12.3 mmol, 1.0 eq),4,4,5,5-tetramethyl-2-(prop-1 -en-2-yl)-1 ,3,2-dioxaborolane [CAS RN: 126726-62-3] (3.10 g, 18.4 mmo[, 1.5 eq), Pd(dppf)C[2.CH2C[2 (502 mg, 0.61 mmo[, 0.05 eq) and cesium carbonate (12.0 g, 36.9 mmo[, 3.0 eq) were dissolved in 130 mL dioxane/water (5/1). The reaction mixture was heated to 90C for 2 h. On cooling, the reaction mixture was partitioned between water anddichloromethane. The organic phase was washed with brine and the phases were separated by the use of a Whatman filter. The volatile components were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 100 g SNAP cartridge: hexane -> hexane/ethyl acetate 9/1) to give 600 mg (25% yield of theory) of the title compound in a round 50% purity(UPLC-area%). The impurity was identified as 2,5-di(prop-1-en-2-yl)pyrazine, that was not expected to interfere in the subsequent reaction step. The material obtained was used without further purification.UPLC-MS (Method 4): R = 1.18 mm; MS (ESI0): m/z = 199 [M].

The synthetic route of 2-Bromo-5-iodopyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); 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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

A round bottomed flask was charged with methyl 6-amino 2,3-dichloro pyrazine 5-carboxylate (Aldrich, 25 g, 112.6 mmol), 2-S-ethyl piperazine (prepared as per Williams et al J. Med. Chem 1996, 39, 1345, 83% active, 15.7 g, 112.7 mmol), cesium carbonate (100 g, 300 mmol) and 1,4 dioxane (400 mL). The flask was equipped with a reflux condenser and heated to 80 C. After 12 hours the reaction was cooled, diluted with CH2Cl2 (200 mL), and filtered through celite. The filtrate was washed once with water and then concentrated to an oil. The crude product was purified by silica gel column chromatography (3% to 10% MeOH in CH2Cl2) to afford compound A3 (30.8 g, 91%). MS:M+H=300

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US2007/82913; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1082843-72-8, 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. 1082843-72-8 name is 6-Bromo-3-chloropyrazin-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.

6-bromo-3-chloropyrazin-2-amine (2g, 9.59 mmol) and methyl 2-hydroxyacetate (2.222 ml, 28.8 mmol) were suspended in Tetrahydrofuran (THF) (88 ml) under N2 at ambient temperature in a multi necked flask. Potassium tert-butoxide 1 M in THF (23.99 ml, 23.99 mmol) was added and the mixture was stirred under N2 and heated to 50C for 18hrs. The reaction was monitored by 2mins liquid chromatography-mass spectrometry (LCMS) (high pH). After 18hrs, starting material still present by LCMS. Potassium tert- butoxide 1 M in THF (9.59 ml, 9.59 mmol) was added and left to stir for an additional 1 hr. (0080) After a total of 19hrs, starting material consumed by LCMS. The mixture was allowed to cool to ambient temperature then partitioned between water (60ml) and ethyl acetate (60ml) (organic layer discarded). The aqueous layer was acidified to pH=4 with aq 2M HCI then extracted twice with ethyl acetate (60ml). The combined organic layers were washed with water (75ml) then dried by passing through a hydrophobic frit and evaporated under vacuum to give the crude material 6-bromo-2H-pyrazino[2,3- b][1 ,4]oxazin-3(4H)-one (1 .9618g, 7.93 mmol, 83 % yield, with a purity of 93 % by NMR) as a red/brown solid. Sample carried through to next step without further purification LCMS (2mins, high pH): V4100473-3 rt = 0.44 mins, MH- = 230 (0081) IH NMR (400 MHz, DMSO-de) d ppm 4.90 (s, 2 H) 7.92 (s, 1 H) 11.81 (s, 1 H)

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALDER, Catherine Mary; EDWARDS, Lee J; HAYES, Jerome; EVANS, Rhodri Ll?r; MCKAY, Blandine Suzanne Jeanne; (21 pag.)WO2019/180634; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 1082843-72-8, 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. 1082843-72-8, name is 6-Bromo-3-chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

6-Bromo- 3-chloropyrazin-2-amine (2000 mg, 9.59 mmol) was dissolved in DCM (48 ml) followed by triethylamine (3.99 ml, 28.78 mmol), di-tert-butyl dicarbonate (4188.12 mg, 19.19 mmol), and N,N-dimethylpyridin-4-amine (87.91 mg, 0.72 mmol). The reaction was allowed to stir at room temperature for overnight. The crude material was washed with water, dried, filtered and concentrated. The crude material was dissolved in minimal DCM and loaded onto a 25 g prepacked silica loader and eluted off a 40 g column using 0-30% MeOH/DCM. The title compound XI was isolated and identified by LCMS and NMR. The product was a mix of mono and bis boc-protected material, mainly bis boc-protected as observed by NMR.

The chemical industry reduces the impact on the environment during synthesis 6-Bromo-3-chloropyrazin-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GILEAD SCIENCES, INC.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KROPF, Jeffrey E.; LEE, Seung H.; LO, Jennifer R.; MITCHELL, Scott A.; SCHMITT, Aaron C.; XIONG, Jin-Ming; XU, Jiangjun; ZHAO, Zhongdong; WO2015/100217; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 313340-08-8,Some common heterocyclic compound, 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, molecular formula is C7H7Cl2N3O, 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 mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (1.0 g) and DMF (15 mL), thionyl chloride (1 mL) was added at room temperature and stirred for 20 minutes. The reaction liquid was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane) to give 3,5-dichloro-6-ethylpyrazine-2-carbonitrile (608 mg) as a slightly yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, its application will become more common.

Reference:
Patent; Waters Technologies Corporation; US2012/40968; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]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 143591-61-1, Quality Control of 3-Bromo-8-chloroimidazo[1,2-a]pyrazine

Ammonia of a 30% (w/v) aqueous solution (2.3 mL, 57.37 mmol)was added to a solution of 3-bromo-8-chloroimidazo [1,2-a]pyrazine(500 mg, 2.15 mmol) in acetonitrile in a microwave-adaptedvial. The reaction was submitted to microwave irradiations during2 h at 140 C. The solvent is removed under reduced pressure. Thecrude mixture was dissolved in ethyl acetate and successivelywashed with saturated aqueous chloride ammonium, distilledwater and finally brine. The organic phase was dried on sodiumsulphate, filtered and concentrated under reduced pressure. Thecompound is obtained as a white solid (87% yield). C6H5BrN4. Mw:213.03 g/mol. Mp 242-243 C. 1H-RMN delta (ppm, 400 MHz, DMSOd6)7.10 (s, 2H, NH), 7.36 (d, 1H, CH 6, J = 8 Hz), 7.56 (d, 1H, CH 7,J = 8 Hz), 7.65 (s, 1H, CH 2). 13C-RMN delta (ppm, 100 MHz, DMSO-d6)97.81 (Cq 1), 108.03 (CH 7), 130.19 (CH 6), 132.45 (CH 2), 133.46 (Cq30), 150.72 (Cq 4). MS (ESI+ , QTof, m/z): 213.1 [M+H]+. HRMScalculated for C6H6BrN4 212.9776, found 212.9785.

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:
Article; Patinote, Cindy; Bou Karroum, Nour; Moarbess, Georges; Deleuze-Masquefa, Carine; Hadj-Kaddour, Kamel; Cuq, Pierre; Diab-Assaf, Mona; Kassab, Issam; Bonnet, Pierre-Antoine; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 909 – 919;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 1458-01-1, These common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, 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.

General procedure: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 957344-74-0, The chemical industry reduces the impact on the environment during synthesis 957344-74-0, name is 5,8-Dibromoimidazo[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

Step 3 (5-Bromoimidazo[l,2-a]pyrazin-8-yl)-(4-(4-methylpiperazin-l-yl)phenylamine[00292] 4-(4-Methylpiperazin-lyl)phenylamine (5 08g, 26 6mmol) and NN- diisopropylethylamine (4 6mL, 26 6mmol) and 5,8-dibromoimidazo[l,2-a]pyrazine (6 Ig, 22 2mmol) in iso-propanol (15OmL), is heated at 900C for 2 days The solvent is removed in vacuo, and the crude residue partitioned between DCM and IN NaOH The organic phase is separated, then washed with water followed by brine. The organic layer is separated, dried (MgSO4) and evaporated. The crude residue is chromatographed on silica gel, eluting with DCM followed by 96:4 DCM NH 3 (7M in MeOH), and the fractions containing the desired product are combined and evaporated The residue is t?turated with Et2theta to afford the title compound as a solid

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, 5,8-Dibromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

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