Pyrazines

Some common heterocyclic compound, 957344-74-0, name is 5,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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. Recommanded Product: 957344-74-0

A mixture of known compound 7 (2.75g, 9.90mmol), cyclopropylamine (3.4mL, 49.50mmol) and N, N-diisopropylethylamine (3.5mL, 19.80mL) in 1,4-dioxane (33mL) was stirred at 100C for 16h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated aqueous NaHCO3. The organic phase was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (Hexanes:EtOAc=1:2) to afford the title compound 9 (2.3g, 92%). 1H NMR (300MHz, DMSO-d6) delta 7.88 (s, 1H), 7.82 (br, 1H), 7.58 (s, 1H), 7.49 (s, 1H), 2.85 (m, 1H), 0.68 (m, 2H), 0.63 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 957344-74-0, its application will become more common.

Reference:
Article; Kang, Seok Jong; Lee, Jung Wuk; Chung, Shin Hyuck; Jang, Sun Young; Choi, Jaeyul; Suh, Kwee Hyun; Kim, Young Hoon; Ham, Young Jin; Min, Kyung Hoon; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 660 – 670;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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. Safety of 3-Amino-6-bromopyrazine-2-carboxylic acid

Step 1. Synthesis of tert-butyl (l-(2-(3-amino-6-bromopyrazine-2-carboxamido)pyridin- 3-yl)-4-methylpiperidin-4-yl)carbamate. In a 100 mL round bottom flask equipped with a magnetic stirrer HBTU (2.23 gm, 5.87 mmol), 3-amino-6-bromopyrazine-2-carboxylic acid (1.17 gm, 5.39 mmol), and N-ethyl-N- isopropylpropan-2-amine (1.28 mL, 7.34 mmol) were allowed to stir in DMF (15 ml) for 15 minutes whereupon tert-butyl (l-(2-aminopyridin-3-yl)-4-methylpiperidin-4-yl)carbamate (1.5 gm, 4.9 mmol) was added in one portion. Reaction was allowed to stir for 16hr. Reaction was then poured into DMF and extracted thrice with 50 mL ethyl acetate. Organic extracts were combined and dried with brine followed by anhydrous sodium sulfate. The residue was purified by silica gel using gradient chromotography ethanol – ethyl acetate 0 -10% which yielded pure tert-butyl (l-(2-(3-amino-6-bromopyrazine-2-carboxamido)pyridin-3-yl)-4-methylpiperidin-4- yl)carbamate (1.86 gm, 67.5% yield) upon evaporation of fractions containing the desired product. LC-MS (Acidic method): ret.time= 1.17 min, M+H = 508.3.

The synthetic route of 3-Amino-6-bromopyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; LUZZIO, Michael Joseph; PAPILLON, Julien; VISSER, Michael Scott; (213 pag.)WO2016/20864; (2016); A1;,
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87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, 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. COA of Formula: C5H4Br2N2O

A mixture of tert-butyl 4-(4-aminophenyl)piperidine-l-carboxylate (2.5 g, 9.06 mmol) and 3,5-dibromo-l-methylpyrazin-2(lH)-one (2.2 g, 8.23 mmol) in isopropanol (30 mL) was heated at 85 °C for 15 h. After the reaction was finished, it was filtered and the solid was washed with isopropanol to afford 282a as a white solid (2.9 g, 80 ).LCMS: (M+H)+ 463

The synthetic route of 87486-34-8 has been constantly updated, and we look forward to future research findings.

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;,
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Application of 21943-17-9,Some common heterocyclic compound, 21943-17-9, name is 5-Bromo-3-chloropyrazin-2(1H)-one, molecular formula is C4H2BrClN2O, 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 solution of 56 (1.50 g, 7.16 mmol), the appropriate secondary amine (8.59 mmol, 1.20 equiv) and diisopropylethylamine (1.50 mL, 8.59 mmol) in n-butanol (15 mL)was heated in a microwave reactor using variable wattage to 140 C for 1 h. The mixture was concentrated and purified by flash column chromatography on silica, eluting with 9:1 dichloromethane/methanol, to give gave 58-63.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-3-chloropyrazin-2(1H)-one, its application will become more common.

Reference:
Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728,16;; ; Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728;,
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Pyrazine | C4H4N2 – PubChem

Related Products of 74290-67-8, 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. 74290-67-8 name is 2-Amino-5-bromo-3-methylpyrazine, 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-methyl-pyrazin-2-amine (1000 mg, 5.32 mmol), phenol (650 mg, 6.91 mmol), Cs2C03 (2600 mg, 7.98 mmol), Cul (203 mg, 1.06 mmol), and Nu,Nu-dimethylgly cine (110 mg, 1.06 mmol) in dioxane (5 mL) was degassed and heated to 90 C under N2 for 12 h. After cooling to room temperature, the mixture was diluted with EtOAc (100 mL) and water (100 mL) and the organic phase collected. The aqueous layer was extracted again with EtOAc (100 mL) and the combined organic layers were dried over anhydrous MgSC^ and concentrated to dryness. The residue was purified by flash column chromatography to give the title compound as a yellow oil (533 mg, 49.8% yield). MS (ESI): mass calcd. for CnHnN30, 201.1; m/z found, 202.1 [M+H]+.

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CAI, Min; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; HAO, Baoyu; KREUTTER, Kevin; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; ZHU, Yaoping; ZHANG, Feihuang; ZHANG, Zheng; XIAO, Kun; (1000 pag.)WO2017/100668; (2017); A1;,
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Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 41110-28-5, name is 3-Methylpyrazine-2-carboxylic acid, 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

Example 1.1: Preparation of 3-methyl-pyrazine-2-carboxylic acid ethyl esterTo a solution of 3-methyl-pyrazine-2-carboxylic acid (10 g) (commercially available) and jV,7V-dimethylformamide (“DMF”) (1 drop) in dichloromethane (20 ml) at ambient temperature was added drop wise oxalyl chloride (2.57 ml). The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated and the residue dissolved in dichloromethane (20 ml). Triethylamine (4.04 ml) was added to this solution followed by drop wise addition of ethanol (10 ml). The reaction mixture was stirred at ambient temperature for one hour and then concentrated. The residue was purified by chromatography on silica gel (eluent: 0-10% v/v ethyl acetate in zso-hexane) to give 3- methyl-pyrazine-2-carboxylic acid ethyl ester (9.85 g). MH+ = 167, RT = 0.73 min (Method A). IH-NMR (400 MHz, CDCl3): 8.61 (d, IH), 8.54 (d, IH), 4.49 (q, 2H), 2.85 (s, 3H), 1.46 (t, 3H) ppm.

The synthetic route of 3-Methylpyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA LIMITED; WILLETTS, Nigel, James; MULHOLLAND, Nicholas, Phillip; WORTHINGTON, Paul, Anthony; AVERY, Alaric, James; WO2010/130970; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, molecular formula is C6H9N3, 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: 91476-80-1

6-chloro-2-(l,l-dimethylethyl)-l,3-benzoxazole-7-sulfonyl chloride (457 mg) was dissolved in 2.5 mL DCM and the solution was cooled to 0 0C. Triethylamine (0.41 mL) was added followed by 5,6,7,8-tetrahydroimidazo[l,2-alpha]pyrazine (201 mg) dissolved in 2.5 mL DCM. The reaction mixture was stirred at 0 0C to room temperature over night. The reaction was quenched with water and extracted with DCM (3×10 mL). The combined organic layers were dried Na2SOzI, filtered and the solvent was removed in vacuo. The crude product was purified by column chromatography eluting with a gradient of 0 to 20% MeOH in DCM yielding 409 mg of product. Rf: 0.57 (10% MeOH in DCM).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 91476-80-1, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/124423; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 25911-65-3, name is 3-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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. HPLC of Formula: C5H4N4

EXAMPLE 4 Synthesis of 3-Amino-6-bromopyrazine-2-carbonitrile (Intermediate 3) To a solution of intermediate 2 (1.7 g, 14 mmol) in acetic acid (40 mL) at RT was added bromine (0.95 mL, 19 mmol) slowly. The resulting mixture was heated at 60 C. for 30 min and then cooled to RT. The mixture was poured into ice water and the resulting solid filtered. After thoroughly washed with water, the title compound was obtained as a yellow solid (2.3 g, 83%). 1H NMR (500 MHz, DMSO-d6): delta 8.44 (s, 1H), 7.60 (br s, 2H). MS (ES+): m/z 199 (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 25911-65-3, its application will become more common.

Reference:
Patent; TargeGen, Inc.; US2007/259876; (2007); 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. 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., SDS of cas: 5521-55-1

A solution of compound 4-6 (0.2 g, 0.3 mmol) in EtOAc (2 mL) was cooled to 0 C, and a solution of HC1 in EtOAc (3 0%, 2 mL) was added. The mixture was stirred at rt until no more gas evolution. The mixture was filtered to afford compound 4-7 as a white solid; the solid was washed with EtOAc (20 mL). A round-bottom flask was charged with compound 4-7, compound 9-1 (0.06 g, 0.4 mmol), EDCI (0.13 g, 0.66 mmol) and HOAT (0.1 g, 0.7 mmol), and then DCM (10 mL) was added under N2. The mixture was cooled to 0 C, and DIPEA (0.2 mL, 1 mmol) was added slowly. After the addition, the resulting mixture was stirred at 30 C for 6 hours. After the reaction was complete, the mixture was quenched with water (10 mL). The resulting mixture was extracted with DCM (10 mL) twice. The combined organic layers were washed with saturated aqueous NaC1 (10 mL) and dried over anhydrous Na2SO4, and then concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE : EtOAc (V:V)= 2:1 to give compound 9-2 (0.180 g, 80%) as a white solid. MS (ESI, pos.ion) m/z: 885.3[M+1] and 1HNIVIR (600 IVIHz, CDC13): 5 10.38 (s, 1H), 9.07 (d, J= 0.8 Hz, 1H), 8.44 (s, 1H), 8.15 (d, J= 6.7 Hz, 1H), 7.85 (d, J= 9.1 Hz, 2H), 7.47 (s, 1H), 7.04 (s, 1H), 6.95 (d, J 9.2 Hz, 1H),5.73 (dd, J= 18.2, 8.7 Hz, 1H), 5.50 (s, 1H), 5.02-4.97 (m, 1H), 4.69-4.64 (m, 2H), 4.49 (d, J= 11.5 Hz, 1H), 4.10 (dd, J = 11.6, 3.9 Hz, 1H), 3.77 (s, 3H), 3.22 (dt, J = 13.7, 6.8 Hz, 1H),2.92-2.86 (m, 1H), 2.71 (dd, J= 13.8, 7.7 Hz, 1H), 2.65 (s, 3H), 2.60 (s, 4H), 2.29-2.25 (m, 1H),2.04-2.00 (m, 1H), 1.91 (dd, J= 7.8, 6.1 Hz, 2H), 1.78-1.71 (m, 1H), 1.66 (dd, J= 9.4, 5.9 Hz,1H), 1.53-1.45 (m, 5H), 1.39 (t, J= 13.5 Hz, 7H), 1.16-1.07 (m, 3H), 0.94-0.86 (m, 2H) ppm.

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; LUO, Huichao; REN, Qingyun; XIONG, Zhimin; LIU, Yang; LEI, Yibo; XIONG, Jinfeng; ZHANG, Jiancun; (123 pag.)WO2016/127859; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 1458-18-0,Some common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, molecular formula is C6H5Cl2N3O2, 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: 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).

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-amino-5,6-dichloropyrazine-2-carboxylate, its application will become more common.

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