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. 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-3-morpholinopyrazin-2-amine

5-bromo-3-morpholin-4-yl-pyrazin-2-ylamine (300 mg, 1 eq) was suspended in EtOH (3 mL) and 2,3-dibromo-n-methylmaleimide (31 1 mg, 1 eq) was added. The reaction mixture was heated under microwave irradiation at 120 C for 4 h. On cooling, the mixture was filtered to give a yellow solid (50 mg,) which was heated at 150 C for 5 min under open air. On cooling, the mixture was purified by automated chromatography (Biotage, eluent: 2% to 10% MeOH in DCM) to obtain the expected product I-20 (22 mg) as a yellow solid.

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; 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

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 41270-66-0 as follows. Computed Properties of C16H11ClN2

In one embodiment of the preparation method of the sirepag intermediate of the present invention, the preparation method of the siriparg intermediate according to the present embodiment is: in a reaction bottle equipped with a reflux tube, a drying tube and a thermometer, adding 5- Chloro-2,3-diphenylpyrazine (30.0 g, 0.11 mol, 1.0 eq.), 4-(isopropylamino)-1-butanol (18.5 g, 0.14 mol, 1.25 eq.), 1, 4-Dioxane 150 mL, stir and dissolve, and then add Pd (dba)2(2.4g, 4.2mmol), P(o-tolyl)3(1.69 g, 8.3 mmol), sodium tert-butoxide (13.0 g, 0.135 mol), heated to 120 C., and incubated for 1.8 hours. The reaction was complete by TLC and the reaction was stopped.The mixture was cooled to room temperature and filtered. The filtrate was adjusted to pH 6.5-7.5 with 1N hydrochloric acid, extracted with ethyl acetate (150 mL x 2), washed with 150 mL of brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure with the residue being ethanol: The mixture was recrystallized with 300 mL of n-hexane = 1:15 mixed solvent and dried in an oven to obtain 39.0 g of a white solid. The yield was 96%, and the liquid purity was 97.1%.

According to the analysis of related databases, 41270-66-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Saifeng Pharmaceutical Technology Co., Ltd.; Feng Wenzhou; Chen Rongmin; Ding Xiaoming; Zheng Yuchun; Bao Changxiao; Gong Zihua; (9 pag.)CN107652243; (2018); 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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., Formula: C6H3Br2N3

To a solution of 6,8-dibromoimidazo[1,2-a]pyrazine (0.50 g, 1.8 mmol) (Combi-Blocks, OR-7964) in DMF (12 mL) was added N-iodosuccinimide (0.45 g, 2.0 mmol). The reaction mixture was then heated at 60 C. for 15.5 h. The reaction mixture was concentrated in vacuo. The resulting solid was taken up into DCM. The organic layer was washed sequentially with water and sat. Na2S2O3 (aq). The organic layer was then dried over Na2SO4, filtered, and concentrated to afford the title compound as a light yellow solid (0.64 g, 88%). LCMS for C6H3Br2IN3 (M+H)+: calculated m/z=401.8, 403.8, 405.8; found 401.8, 403.7, 405.6.

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; Incyte Corporation; Buesking, Andrew W.; Sparks, Richard B.; Combs, Andrew P.; Douty, Brent; Falahatpisheh, Nikoo; Shao, Lixin; Shepard, Stacey; Yue, Eddy W.; (269 pag.)US2018/9816; (2018); 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., Product Details of 1458-18-0

To a stirred mixture of methyl 3-amino-5, 6-dichloropyrazine-2-carboxylate (600 mg, 2.702 nMol, 1 equiv) and phenylboronic acid (336.09 mg, 2.756 nMol, 1.02 equiv) in dioxane (20 mL) were added K 3PO 4 (1147.23 mg, 5.405 nMol, 2 equiv) and Pd (dppf) Cl 2 (395.46 mg, 0.540 nMol, 0.2 equiv) in portions at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 3 h at 70 under nitrogen atmosphere. The resulting mixture was concentrated under reduced pressure. The residue was purified by Prep-TLC (PE/EtOAc 1: 1) to afford methyl 3-amino-6-chloro-5-phenylpyrazine-2-carboxylate (400 mg, 56.14%) as a yellow solid. LCMS: m/z (ESI) , [M+H] + = 264.3. 1H NMR (400 MHz, DMSO-d 6) delta 3.89 (3H, s) , 7.53 (3H, dd) , 7.61 (2H, s) , 7.71 -7.78 (2H, m)

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

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; QI, Changhe; TSUI, Honchung; ZENG, Qingbei; YANG, Zhenfan; ZHANG, Xiaolin; (399 pag.)WO2020/35052; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 110223-15-9, A common heterocyclic compound, 110223-15-9, name is 2-Amino-3-benzyloxypyrazine, molecular formula is C11H11N3O, 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.

2-Bromo-3-oxo-butyric acid ethyl ester (15.6 g, 74.6 mmol) was added to a solution of 2-amino-3-benzyloxypyrazine (Compound m in Scheme 1, 5 g, 24.9 mmol) in ethanol (20 mL). The reaction mixture was refluxed for 5 h. The reaction mixture was allowed to cool to r. t. and an off- white coloured solid precipitated out. The solid was collected and washed with ice-cold ethanol to give a white solid (1.08 g, 66%). 1H-NMR (DMSO-d6) No. 11.6 (br s, 1H), 7.97 (d, J5.7 Hz, 1H), 7.00 (t, J 5. 8-Hz, 1H), 4.35 (q, J 7.1 Hz, 2H), 2.52 (s, 3H), 1.34 (t, J 7.1 Hz, 3H); MS (ESI) 222.0 ([M+H])

The synthetic route of 110223-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CARDIOME PHARMA CORPORATION; WO2005/34837; (2005); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, molecular formula is C6H3BrClN3, 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. SDS of cas: 143591-61-1

[00274] 3-(Trifluoromethyl)phenol (1.57 mL, 12.95 mmol) was added to a suspension of sodium hydride (706 mg, 17.65 mmol – 60% in mineral oil) in anhydrous DMF (30 mL) and the resulting mixture was stirred for 40 minutes. A solution of 3-bromo-8-chloroimidazo[l,2- ajpyrazine (2.731 g, 11.75 mmol) in anhydrous DMF (30 mL) was added to the reaction mixture and stirred overnight at room temperature. The reaction mixture was diluted with water and the resulting precipitate was filtered off and washed with water and then hexane to give 3-bromo-8-(3-(trifluoromethyl)phenoxy)imidazo[l,2-a]pyrazine (3.4g, 81%) as a white solid. LCMS MH+ 359.8. 1H NMR (d6-DMSO): 8.20 (IH, d, J 4.7), 7.96 (IH, s), 7.64-7.77 (4H, m), 7.52 (IH, d, J4.7).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 143591-61-1, its application will become more common.

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; PRICE, Paul Damien; MIDDLETON, Penny; WO2010/69684; (2010); 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., Application In Synthesis of Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

General procedure: To a solution of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (1.0 eq.) in 2-propanol (5 mL/mmol), an appropriate primary or secondary amine(3-6 eq.) was added, and the reaction mixture wasrefluxed for 2 h.10) The solution was cooled to roomtemperature, concentrated under reduced pressure, andthe residue was purified by silica-gel column chromatography(Wako gel C-200, 30-40% ethyl acetate/n-hexane) to afford the series 1 intermediate (yield:32-95%). The regioselectivity of the nucleophilicsubstitution at the 5-position of the pyrazine ring wasconfirmed by an X-ray structural analysis (Fig. S1).

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

Reference:
Article; Murai, Masatoshi; Habu, Sayako; Murakami, Sonomi; Ito, Takeshi; Miyoshi, Hideto; Bioscience, Biotechnology and Biochemistry; vol. 79; 7; (2015); p. 1061 – 1066;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 25710-18-3, A common heterocyclic compound, 25710-18-3, name is 2,3-Dichloropyrido[2,3-b]pyrazine, molecular formula is C7H3Cl2N3, 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: A mixture of 2,3-dichloropyrazine or its derivatives (1, 1.0 equiv), substituted phenols (2a-p) (1.0 equiv) and anhydrous AlCl3 (1.0 equiv) in dichloroethane (5 mL) was stirred at 80 oC for 30 min. Then the mixture was cooled to room temperature and additional quantity of AlCl3 (1.0 equiv) was added. The mixture was stirred again at 80 oC for another 30 min. After completion of the reaction, the mixture was poured into ice-cold water (15 mL), stirred for 10 min and then extracted with ethyl acetate (3.x.5 mL). The organic layers were collected, combined, washed with water (3.x.10 mL), dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to afford the expected products.

The synthetic route of 25710-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, K. Shiva; Adepu, Raju; Kapavarapu, Ravikumar; Rambabu; Krishna, G. Rama; Reddy, C. Malla; Priya, K. Krishna; Parsa, Kishore V.L.; Pal, Manojit; Tetrahedron Letters; vol. 53; 9; (2012); p. 1134 – 1138;,
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 24241-18-7 as follows. COA of Formula: C4H3Br2N3

Step 1: synthesis of 3-amino-6-bromopyrazine-2-carbonitrile (14) A solution of copper(i) cyanide (1.20 g, 13.42 mmol) and sodium cyanide (0.658 g, 13.42 mmol) in DMF (10 mL) was heated to 125 C. 2-amino-3,5-dibromo pyrazine (2.61 g, 10.32 mmol) was added in portions. The reaction was stirred at 125 C., and after 5 h quenched in ice cold NaHCO3 solution. The black precipitate was filtrated off and the filtrate was extracted (3*) with EtOAc. The organic layer was washed with brine, dried and evaporated. Purification by chromatography (CH2Cl2) gave pure 3-amino-6-bromopyrazine-2-carbonitrile 14 (1.38 g, 67.2%). 1H-NMR (400 MHz, CDCl3) 5.29 (br s, 2H), 8.30 (s, 1H). (m/z)=199 and 201 (M+H)+.

According to the analysis of related databases, 24241-18-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Folmer, Brigitte Johanna Bernita; Man, de Adrianus Petrus Antonius; Gernette, Elisabeth Sophia; Corte Real Goncalves Azevedo, Rita; Ibrahim, Hemen; US2013/79341; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1049026-49-4, A common heterocyclic compound, 1049026-49-4, name is 2-Bromo-5-(methylthio)pyrazine, molecular formula is C5H5BrN2S, 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.

Step B: 2-bromo-5-(methylsulfonyl)pyrazine: An aqueous solution of Oxone (4.0 g, 6.6 mmol,3.13 mL) was added dropwise to a methanol solution of 2-bromo-5-(methylsulfanyl)pyrazine(450 mg, 2.2 mmol, 19 mL) at ambient temperature. The reaction mixture was stirred for 3hours, filtered over a pad of CELITE and then organic layer was concentrated in vacuo. The crude residue was purified via MPLC (0-100% EtOAc/hexane gradient) to afford titlecompound.

The synthetic route of 1049026-49-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP; TANG, Haifeng; PIO, Barbara; JIANG, Jinlong; PASTERNAK, Alexander; DONG, Shuzhi; FERGUSON, Ronald Dale, II; GUO, Zack Zhiqiang; CHOBANIAN, Harry; FRIE, Jessica; GUO, Yan; WU, Zhicai; YU, Yang; WANG, Ming; WO2015/17305; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem