Tag: M.W=200-300

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 486424-37-7 as follows. Application In Synthesis of 3-Amino-6-bromopyrazine-2-carboxylic acid

To the 3L into the reaction bottle 50.1g II, 2L methanol. 0 – 5 C lower, to the slowly dropping 133g 98.3% concentrated sulfuric acid, then completing, heating up to 40 C, instead on invitation 48h to raw material II basic reaction end. turns on lathe does methanol, 0 – 5 C lower, adding 200 ml methanol, 500g ice water mixture, wherein the aqueous solution of sodium bicarbonate to pH=6 – 7 adds by drops full and adjusted to. Filtering, the filter cake 45 C vacuum drying 12h, get 43.2g brown solid III, yield 80.1%

According to the analysis of related databases, 486424-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing Huawei Pharmaceutical Development Co., Ltd.; Bao Jinyuan; Huang Hui; Jiang Yuwei; Zhang Xiaoqing; (8 pag.)CN104496917; (2017); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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 486424-37-7, category: Pyrazines

The 3-(lH-benzimidazol-2-yl)-5-bromopyrazin-2-amine used as a starting material was prepared as follows :-etaATU (7.3 g) was added to a mixture of 3-amino-6-bromopyrazine-2-carboxylic acid (4 g), 1,2-phenylenediamine (2.07 g), triethylamine (3.8 ml) and DMF (40 ml) and the reaction mixture was stirred at ambient temperature for 1 hour. The resultant mixture was poured into aqueous sodium hydrogen carbonate solution and the resultant precipitate was isolated. The material so obtained was dissolved in acetic acid (20 ml) and heated to 900C for 3 hours. The resultant mixture was evaporated and the residue was triturated under methylene chloride. There was thus obtained 3-(lH-benzimidazol-2-yl)-5-bromopyrazin-2-amine (2.7 g); NMR Spectrum: (DMSOd6) 7.29 (m, 2eta), 7.59 (d, IH), 7.76 (d, IH), 8.28 (s, IH), 13.05 (s, IH); Mass Spectrum: M-HH+ 292; RT 2.34 min.

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; ASTRAZENECA AB; WO2009/7390; (2009); A2;,
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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.

Step 1 A mixture of methyl 3,5-dichloropyrazine-2-carboxylate (1.30 g, 6.28 mmol) and sodium methoxide (0.5 M in MeOH, 13.8 mL) was stirred at room temperature for 2 h. The mixture was quenched with ice water and extracted with EtOAc (2 x). The combined extracts were dried over sodium sulfate, filtered and concentrated. Si02 column chromatography (5% to 100% EtOAc in hexane) in vacuo to afford compound 2K-2. MS for 2K-2: m/e = 203 (M+l).

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; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CUMMING, Jared, N.; HE, Shuwen; TAOKA, Brandon, M.; TRUONG, Quang, T.; WU, Wen-Lian; (122 pag.)WO2015/187437; (2015); A1;,
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Synthetic Route of 25710-18-3, The chemical industry reduces the impact on the environment during synthesis 25710-18-3, name is 2,3-Dichloropyrido[2,3-b]pyrazine, I believe this compound will play a more active role in future production and life.

To a stirred solution of 4.5 g of compound 3 (22.5 mmol) in 10 mL of acetonitrile, 2.5 mL of phenylacetylene (23.0 mmol), 25 mL of triethylamine (TEA; 180 mmol), 500 mg of palladium(II) acetate (2.2 mmol), 419 mg of copper iodide (2.2 mmol), and 577 mg of triphenylphosphine (2.2mmol) were added, and the mixture was heated up to 80 ¡ãC for 3 h. The resulting mixture was concentrated, dried under vacuum, and extracted with a mixture of EtOAc and water.The organic layer was separated, washed with water, and dried over MgSO4. After the removal of the solvent by a rotary evaporator, the residue was purified by column chromatography using (EtOAc: n-hexane = 1:4) to achieve compound 4 as a yellow solid with 68percent yield

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, 2,3-Dichloropyrido[2,3-b]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Park, Jeong Hoon; Kim, Heejung; Kim, Dong-Yeon; Yang, Seung Dae; Hur, Min Goo; Kim, Sang Wook; Yu, Kook Hyun; Bulletin of the Korean Chemical Society; vol. 36; 7; (2015); p. 1778 – 1783;,
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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

To a suspension of N-(3-aminobicyclo[l . l . l]pentan-l-yl)-2-(3,4- dichlorophenoxy)acetamide hydrochloride (0.08 g, 0.237 mmol, Example 2B) in N,N- dimethylformamide (0.5 mL, 6.46 mmol) was added N,N-diisopropylethylamine (0.166 mL, 0.948 mmol) followed by 2-bromo-5-(trifluoromethyl)pyrazine (0.065 g, 0.284 mmol). The reaction mixture was stirred overnight at 90 C. It was then concentrate under reduced pressure at 50 C. The residue was purified by flash column chromatography on silica gel (24 g) eluted with heptane and ethyl acetate (0 to 100%) to give 40 mg of the title compound (35.9% yield) as a white solid. JH NMR (400 MHz, DMSO-<) delta ppm 8.78 (s, 1H), 8.59 (s, 1H), 8.44 (s, 1H), 7.99 (s, 1H), 7.55 (d, J = 8.8 Hz, 1H), 7.27 (d, J = 2.8 Hz, 1H), 6.99 (dd, J = 9.0, 2.9 Hz, 1H), 4.51 (s, 2H), 2.37 (s, 6H). 19F NMR (376 MHz, DMSO-<) delta ppm -64.83; MS (ESI+) mJz 447 (M+H)+. 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; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); A1;,
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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. 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

(3R)-3-te/-t-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyric acid (40 g, 0.12 mol) was dissolved in dimethylformamide (DMF)(240 mL) at room temperature while the reaction flask was under N2, then, cooled with ice bath and stirred for 30 minutes. In a different flask, DCC (32.21 g, 0.16 mol) was dissolved in DMF (160 mL) to obtain a 200 mL solution. To the (3R)-3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro- phenyl)-butanoic acid solution was added 70 mL from the DCC solution drop-wise, 3- (trifluoromethyl)-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyrazine hydrochloride (32.94 g, 0.14 mol) and Et3N (24.82 g, 0.24 mol). The reaction was stirred for 10 minutes, then, DMAP was added (8.8 g, 0.07 mol). The reaction was stirred for 2 hours, then, 65 mL of DCC solution was added drop-wise, and after another 1 hour of stirring in an ice bath, the last 65 mL of DCC solution was added drop- wise. The reaction was stirred at room temperature over night. The mixture was filtrated by vacuum filtration and washed with DMF 2X50 mL. The solvent was evaporated and EtOAc was added (1400 mL), the organic phase washed with 90 mL of 5% citric acid, 60 mL of 10% citric acid, and 100 mL of saturated NaHCO3, dried over Na2SO4 and evaporated to yield a beige solid. The product was dissolved in IPA (300 mL) by heating to reflux. When the solution became clear-yellow the solution was cooled to room temperature and stirred over night. The product was isolated by vacuum filtration, washed isopropanol, and dried in a vacuum oven at 4O0C overnight to obtain tert-butyl (R)-4-(3-(trifluoromethyl)-5,6-dihydro- [l,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-l-(2,4,5-trifluorophenyl)-4-oxobutan-2-yl- carbamate (52 g, 85 % yield).

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; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2009/64476; (2009); 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. 957230-70-5, name is 3,6-Dibromopyrazin-2-amine, A new synthetic method of this compound is introduced below., Quality Control of 3,6-Dibromopyrazin-2-amine

Step 2 5 ,8-Diotabromo-3-methyliotamiotadazo[ 1 ,2 ajpyrazine[00298] 2,5-Dibromo-3-aminopyrazme (2 0 g, 7 9 mmol), 2-bromo-l,l -dimethoxypropane (7 25 g, 40 0 mmol) and py?dimum p-toluenesulfonate (2 0 g, 7 9 mmol) are stirred in acetomtrile (65 mL) at reflux for 3 days The mixture is cooled and the solvent evaporated under reduced pressure The residue is partitioned between DCM (150 mL) and water (50 mL) and the layers separated The organic fraction is washed with NaHCtheta3 (sat aq , 50 mL) and b?ne (50 mL) and d?ed over MgStheta4 Evaporation of the solvent under reduced pressure gives a viscous black oil (2 14 g) which is purified by silica chromatography, elutmg with 10% – 20% EtOAc in cyclohexane to afford the title compound as a red-brown solid (280 mg, 1 mmol)

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

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

Synthetic Route of 76537-18-3, 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 76537-18-3 as follows.

A mixture of 3-bromo-5-chloropyrazin-2-amine (545 mg, 2.61 mmol, D-L Chiral Chemicals) and [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride (178 mg, 0.261 mmol) in DMA (18.2 mL) was degassed. Separately, a vial was charged with zinc (freshly activated and dried according to the procedure found in WO2011/143365, 1.49 g, 22.8 mmol) and the vial was flushed with N2 and heated with a heat gun, then cooled. Dry THF (20 mL) was added. 1,2-Dibromoethane (0.20 mL, 2.4 mmol) was added and the mixture was heated with a heat gun to reflux, and then cooled to room temperature. This heating and cooling cycle was performed three times. TMSCl (0.60 mL, 4.7 mmol) was added. The mixture was heated to 50 C. in an oil bath, and ethyl 3-iodocyclobutane-1-carboxylate (2.0 g, 7.9 mmol, prepared as described in WO2014/200882, the disclosure of which is incorporated herein by reference in its entirety) in THF (10 mL) was added dropwise. The mixture was maintained at 50 C. for about 1 hour, then was cooled to room temperature and degassed by bubbling a stream of nitrogen through the mixture for 5 min. This mixture was then added to the solution of 3-bromo-5-chloropyrazin-2-amine above, excluding zinc solids. The reaction was heated to 50 C. for 1.75 hours, then to 80 C. for 45 minutes. Upon cooling to room temperature, the reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted again with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The product was purified via flash chromatography, eluting with a gradient from 0-75% EtOAc in hexanes to afford product (0.35 g, 52%). The cis- and trans-isomers are partially separable, however the product was carried as a mixture to the following step. LCMS calculated for C11H15ClN3O2(M+H)+: m/z=256.1, found: 256.0. First diastereomer to elute: 1H NMR (400 MHz, CDCl3) delta 7.97-7.73 (s, 1H), 4.64-4.32 (s, 2H), 4.29-4.14 (q, J=7.1 Hz, 2H), 3.72-3.52 (m, 1H), 3.27-3.10 (m, 1H), 2.80-2.51 (m, 4H), 1.35-1.25 (t, J=7.1 Hz, 3H). Second diastereomer to elute: 1H NMR (400 MHz, CDCl3) delta 7.98-7.78 (s, 1H), 4.59-4.45 (s, 2H), 4.21-4.12 (q, J=7.1 Hz, 2H), 3.47-3.35 (p, J=8.8 Hz, 1H), 3.26-3.15 (m, 1H), 2.77-2.57 (m, 4H), 1.31-1.25 (t, J=7.2 Hz, 3H).

According to the analysis of related databases, 76537-18-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Incyte Corporation; Shepard, Stacey; Combs, Andrew P.; Falahatpisheh, Nikoo; Shao, Lixin; (96 pag.)US2019/276435; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 143591-61-1, These common heterocyclic compound, 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, 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.

3-bromo-8-chloroimidazo [1,2-a] pyrazine (1.33 g, 5.7 mmol),1- (2-methoxyethyl) -1H-pyrazole-4-amine (0.96 g, 6.8 mmol) was added to 15 mL of n-butanol,The temperature was raised to 120 C and reacted overnight.The solvent was removed by rotary evaporation, diluted with 30 mL of water, and extracted with ethyl acetate (20 mL * 3). The organic phases were combined,It was washed with 20 mL of saturated brine, dried over anhydrous sodium sulfate, and concentrated.Separation through a silica gel column gave 1.45 g of a pale yellow solid with a yield of 76%.

The synthetic route of 143591-61-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Xing Qingfeng; Ai Yixin; (85 pag.)CN110272426; (2019); A;,
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. 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3,5-Dichloro-6-ethylpyrazine-2-carboxamide

A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (3a, 90 mg, 0.409 mmol), 3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline (124 mg, 0.407 mmol), DIPEA (71 muL, 0.408 mmol) and 1,4-dioxane (3.6 mL) was stirred at 110 C for 19 h. After the mixture was cooled, water was added, and the resulting slurry was extracted with EtOAc. The organic layer was dried over Na2SO4, andconcentrated in vacuo. The residue was purified by silica gel columnchromatography (CHCl3/MeOH) to give 11 (110 mg, 55%) as an ochersolid. 1H NMR (CDCl3): delta 1.28 (3H, t, J=7.4 Hz), 1.72-1.99 (4H, m),2.29 (3H, s), 2.34-2.78 (11H, m), 2.85 (2H, q, J=7.5 Hz), 3.44-3.59(2H, m), 3.89 (3H, s), 5.38-5.57 (1H, m), 6.90 (1H, d, J=8.4 Hz),7.08-7.19 (1H, m), 7.32-7.41 (1H, m), 7.62-7.80 (1H, m), 10.66 (1H,s); MS (ESI) m/z [M+H]+ 488, 490.

According to the analysis of related databases, 313340-08-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iikubo, Kazuhiko; Kurosawa, Kazuo; Matsuya, Takahiro; Kondoh, Yutaka; Kamikawa, Akio; Moritomo, Ayako; Iwai, Yoshinori; Tomiyama, Hiroshi; Shimada, Itsuro; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1683 – 1692;,
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Pyrazine | C4H4N2 – PubChem