Tag: M.W=200-300

Electric Literature of 622392-04-5,Some common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, molecular formula is C4H2BrIN2, 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.

(l-((l-(Trifluoromethyl)cyclobutyl)methyl)piperidin-4-yl)methanol (0.88 g, 3.50 mmol) was dissolved in THF (30 mL). At 0C, NaH (0.13 g, 5.25 mmol) was added thereto. The mixture was stirred for 30 minutes. 2-bromo-5-iodopyrazine (1.09 g, 3.85 mmol) was added thereto, followed by stirring at 55C for 10 h. To the reaction mixture, water was added, and the mixture was extracted with EtOAc. The organic layer was washed with saturated brine aqueous solution, dried with anhydrous MgS04, and then concentrated under reduced pressure. The obtained product was used without further purification. (1.40 g, 87%, colorless oil).

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-5-iodopyrazine, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; KIM, Yuntae; LEE, ChangSik; CHOI, DaeKyu; KO, MooSung; HAN, Younghue; KIM, SoYoung; MIN, JaeKi; KIM, DoHoon; WO2015/80446; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 762240-92-6,Some common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, molecular formula is C6H8ClF3N4, 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 triazole base 1 (0.75g, 3.3mmol) in acetonitrile (15mL) at 5AC was added triethylamine (0.96mL, 6.9mmol) followed by ethylmalonyl chloride (0.45mL, 3.5mmol) over 5min. After being stirred for lOmin the reaction mixture was allowed to self warm to EPO room temperature and stirred for a further 90min. The reaction mixture was diluted with ethyl acetate and washed with IN HCl(aq). The aqueous phase was back extracted with ethyl acetate and the organic phases combined, dried over MgSO4 and evaporated. The residue was purified on silica, eluting with ethyl acetate to give amide 2 (0.76g, 76%) as a 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-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, its application will become more common.

Reference:
Patent; PEAKDALE MOLECULAR LIMITED; MADDAFORD, Adrian; GLEN, Rebecca; LEESE, David, Paul; HART, Terance, William; WO2008/40974; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1053656-22-6, name is 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, 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 1053656-22-6, Recommanded Product: 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate

To a chloroform solution (250 ML) of ethyl 7- (TERT-BUTOXYCARBONYL)-5, 6,7, 8- tetrahydroimidazo [1, 2-a] pyrazine-2-carboxylate from Example 10, Step A (18.4 g, 94 mmol), bromine (45 g, 281 mmol) was added, and the mixture was stirred at room temperature for an hour. An aqueous solution of sodium bisulfite was then added and the product was extracted with two 100-ML portions of dichloromethane. The combined organic extracts were washed sequentially with sodium bicarbonate and brine, then dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, gradient elution, 50% ethyl acetate/hexane to 100% ethyl acetate) to give the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2004/58266; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1208082-91-0, name is 6,8-Dibromo-2-methylimidazo[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 1208082-91-0, Quality Control of 6,8-Dibromo-2-methylimidazo[1,2-a]pyrazine

A mixture of Intermediate 1-05 (1.75 g, 6.015 mmol), morpholine (0.526 mE, 6.015 mmol) and DCM (20 mE) was stirred at rt for 16 h. Additional morpholine (0.52 6 mE,6.015 mmol) was added and the mixture was stirred at rt for18 h more. Na2CO3 sat. aq. was added. The organic phase was separated, dried (Na2SO4), filtered and evaporated till dryness to obtain 1.8 g of intermediate 1-10 (Y: quantitative). The resulting product was used in the next step without further purification.

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; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); Serrano Marugan, Manuel; Pastor Fernandez, Joaquin; Martinez Gonzalez, Sonia; Ortega Molina, Ana; Bischoff, James R.; Oyarzabal Santamarina, Julen; (220 pag.)US9993554; (2018); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, 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. Quality Control of 5-Bromo-3-morpholinopyrazin-2-amine

Preparation of Intermediate I-35. Intermediate I-02 (2 g, 7.72 mmol) and methyl 4-chloroacetoacetate (3.56 mL, 30.88 mmol) were heated in two sealed tubes (half of material in each tube) at 90 C. for 2 h. Volatiles were removed under reduced pressure and the residue was purified by flash chromatography on silica gel (c-Hex/EtAOAc 10:0 to 6:4) to obtain a solid that was washed with diethyl ether to render the desired product I-35 (1.17 g, Y: 49%).

The synthetic route of 117719-17-2 has been constantly updated, and we look forward to future research findings.

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

1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, 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: C6H7ClN4O2

To a suspension of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid methyl ester (10.0 g, 49.35 mmol) in methanol (5 mL) was added lithium hydroxide solution (4.17 g, 98.7 mmol in 40 mL water) at room temperature. The reaction was heated to 50 °C and stirred for 2-3 h. The temperature was lowered to room temperature and the reaction stirred overnight. The resulting precipitate was collected by filtration and dried under vacuum to yield 5 (11.3 g, 97percent). Mass (m/z): 187 [M-Li].

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

Reference:
Patent; THE CALIFORNIA INSTITUTE FOR BIOMEDICAL RESEARCH; SCHULTZ, Peter G.; CHATTERJEE, Arnab K.; KUMAR, Manoj; WELZEL, Gustav; WO2015/3083; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

957230-70-5, name is 3,6-Dibromopyrazin-2-amine, 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. name: 3,6-Dibromopyrazin-2-amine

Step 1: N’-(3,6-Dibromo-pyrazin-2-yl)-N,N-dimethylformamidine(D) A mixture of 3,6-dibromo-pyrazin-2-ylamine (15.37 g, 60.80 mmol) and N,N-dimethylformamide dimethyl acetal (10.1 mL, 76.00 mmol), suspended in ethanol (150 mL), is refluxed for 2 hours. The reaction mixture is evaporated in vacuo affording the title compound. 1H-NMR (400 MHz, CDCl3) delta (ppm) 3.20 (s, 3H), 3.21 (s, 3H), 7.93 (s, 1H), 8.48 (s, 1H). LCMS: Rt 3.81 min (99.1%), m/z (APCI) 307 (M+H)+.

The synthetic route of 957230-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Andrews, Martin James Inglis; Chambers, Mark Stuart; Van De Poel, Herve; Bar, Gregory Louis Joseph; US2009/286798; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1458-01-1,Some common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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.

Method D To a suspension of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid methyl ester (10.9 g, 53.7 mmol) in 220 ml 1,4-dioxane and water (40 ml) was added 2-chloro-5-methoxybenzene boronic acid (20 g, 107 mmol), cesium carbonate (17.5 g, 53.7 mmol) and palladium tetrakis(triphenylphosphine) (620 mg, 0.54 mmol). The reaction was heated in an oil bath at 70-75° C. for 2 hours. The reaction was then cooled and poured into 500 ml water. The resulting slurry was stirred for 10 minutes before filtering under vacuum. The beige solid collected was then slurried in 100 ml methanol, stirred for 15 minutes, then filtered, washing the filter cake with methanol and vacuum drying to afford 17.4 g of the title product. 1H-NMR (d6-DMSO): NMR (DMSO): 3.65 (s, 3H), 3.75 (s, 3H), 6.4 (br s 2H), 6.9 (d, 1H), 7.0 (dd, 1H), 7.05 (br, s, 2H), 7.4 (d, 2H). LCMS Rt=3.74 min MS m/z 309 [MH]+

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-diamino-6-chloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; Pfizer Limited; US2007/105872; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, molecular formula is C5H4Br2N2O, 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

A microwave vial equipped with a magnetic stirrer was charged with 3,5-dibromo-l- methylpyrazin-2(lH)-one (1.97 g, 7.4 mmol), 4-morpholinobenzenamine (1.97 g, 11.1 mmol), and isopropanol (25 mL). The system was evacuated and then refilled with N2. It was heated at 90°C for 16 h. Then, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash column chromatography eluting with 5: 1 petroleum ether/ethyl acetate to afford 122a (2.3 g, 85percent). LCMS: [M+H]+ 365.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 87486-34-8, its application will become more common.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); 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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, A new synthetic method of this compound is introduced below., name: 2-Bromo-5-(trifluoromethyl)pyrazine

Step 25 A: 2-[(3R.5R)-3.5-dimethylpiperazin-l -yll-5-(trifluoromethyl)pyrazine (0923) To a solid mixture of (2R,6R)-2,6-dimethylpiperazine dihydrochloride (0924) (0.08 g, 0.44 mmol, 1.0 eq), sodium fert-butoxide (0.21 g, 2.2 mmol, 5.0 eq) and bis(tri- ter/-butylphosphine)palladium(0) (34 mg, 0.07 mmol, 0.15 eq) was added dioxane (4 mL) followed by 2-bromo-5-(trifluoromethyl)pyrazine (0.10 g, 0.44 mmol, 1.0 eq) and the reaction mixture stirred at 50C overnight. The resulting suspension was filtered thru a pad of celite using EtOAc and concentrated. Silica gel column (24 g) was loaded using methylene chloride and run using an increasing gradient of MeOH (0-20%) in methylene chloride over 25 min. Following concentration of the product eluents, 2- [(3R,5R)-3,5-dimethylpiperazin-l-yl]-5-(trifluoromethyl)pyrazine 25a (0.09 g, 0.33 mmol, 75%) was isolated as a yellow oil.

The synthetic route of 1196152-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; HARRIOTT, Nicole; PAGANO, Nicholas; (135 pag.)WO2017/79641; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem