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. 5900-13-0, name is 5-Bromo-3-methoxypyrazin-2-amine, A new synthetic method of this compound is introduced below., Safety of 5-Bromo-3-methoxypyrazin-2-amine

To a stirring solution of 5-bromo-3-methoxypyrazin-2-amine (1.50 g, 7.35 mmol) in pyridine (15 mL), DMAP (15 mg, 0.12 mmol) and (3,5-dichlorophenyl)methanesulfonyl chloride (1.91 g, 7.34 mmol) was added. The reaction was left stirring at room temperature under nitrogen for 2 hrs. A further addition of (3,5-dichlorophenyl)methanesulfonyl chloride (0.20 g, 0.77 mmol) was added to the reaction mixture which was then left stirring for 1 hr at room temperature. The reaction mixture was concentrated in vacuo resulting in a viscous orange mixture which was then diluted with EtOAc (100 mL), washed with water (2 x 80 mL), the organic layer was dried over Na2S04 and concentrated in vacuo to afford an orange solid. This was dissolved in EtOAc (30 mL) and acidified with HCl (2M, 20 mL) which resulted in the precipitation of the title compound as a white solid . The organic and aqueous layer were subsequently separated, the organic layer was washed with water (3 x 30 mL), dried over Na2S04 and concentrated in vacuo to afford a second crop of the title compound as an orange solid (combined yield 1.73g, 54%); H NMR (500 MHz, DMSO) delta 3.93 (s, 3H), 4.88 (s, 2H), 7.36 (d, 2H), 7.63 (m, 1H), 8.12 (s, 1H), 10.80 (s, 1H).

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; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1159811-97-8, 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 1159811-97-8 as follows.

6-Bromo-2-methylimidazo[1,2-a]pyrazine (5 g, 23.58 mmol) and sodium acetate (9.67 g, 117.9 mmol) were dissolved in acetic acid (25 mL) and water (25 mL). Aqueous formaldehyde (37%, 18 mL, 241.77 mmol) was added and the reaction mixture wasstirred at 80C for 1 h, then left to stand at room temperature for 15 h. The reaction mixture was stirred at 80C for a further 4 h, then left to stand room temperature for 15 h. The solid that formed was collected by filtration and washed with water (30 mL). A second batch of solid was obtained from the filtrate and washed with water (30 mL). A third batch of solid was obtained from the filtrate and washed with water (30 mL). Thesolids were combined and dried in vacuo to afford the title compound (4.31 g, 75.5%) as a white solid. H (500 MHz, DMSO-d6) 8.80 (d, J 1.1 Hz, 1H), 8.68 (d, J 1.2 Hz, 1H), 5.29 (t,J5.5 Hz, 1H), 4.81 (d,J5.2 Hz, 2H), 2.43 (s, 3H). LCMS m/z242.

According to the analysis of related databases, 1159811-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; ALEXANDER, Rikki Peter; BENTLEY, Jonathan Mark; BRACE, Gareth Neil; BROOKINGS, Daniel Christopher; CHOVATIA, Praful Tulshi; DEBOVES, Herve Jean Claude; JOHNSTONE, Craig; JONES, Elizabeth Pearl; KROEPLIEN, Boris; LECOMTE, Fabien Claude; MADDEN, James; MILLER, Craig Adrian; PORTER, John Robert; SELBY, Matthew Duncan; SHAW, Michael Alan; VAIDYA, Darshan Gunvant; YULE, Ian Andrew; WO2015/86506; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 1053656-22-6, name is 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, molecular formula is C14H21N3O4, 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

[0097] Method C-Step j: Preparation of ethyl 5,6,7,8-tetrahydroimidazo[l,2-a] pyrazine-2- carboxylate [0098] 7-Tert-butyl 2-ethyl5,6-dihydroimidazo[l,2-a]pyrazine -2,7(8H)-dicarboxylate (50 mg, 0.17 mmol) was dissolved in 3 mL of 3M HCl in ethyl acetate. The mixture was stirred at room temperature for 3 hours. The reaction mixture was filtered and washed with ethyl acetate. The solid was dissolved in water and added saturated NaHCC>3 aqueous solution until pH = 7. The solution was applied to reverse phase chromatography to afford the final compound as a white solid (27.53 mg, 83%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1053656-22-6, its application will become more common.

Reference:
Patent; ZHANG, Xiaohu; WO2014/113191; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 486424-37-7, 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.

METHOD 11; Example 305; Synthesis of tert-butyl l-(3-(3-amino-6-bromopyrazine- 2-carboxamido)pyridin-4-yl)prperidin-3-ylcarbamate [0242] A solution containing 1 eq each of tert-butyl l-(3-aminopyridin-4- yl)piperidin-3-ylcarbamate, S-amino-beta-bromopyrazine-l-carboxylic acid, HOAT and EDC in DMF, at a concentration of 0.5 M, was stirred for 60 hours. The solution was diluted with EtOAc and was washed with H2O (4x), NaCl(sat.), was dried over MgSO4, was filtered and the volatiles were removed in vacuo. After purification by silica gel chromatography (EtOAc eluant), tert-butyl l-(3-(3-amino-6-bromopyrazine-2- carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate was obtained (78%). LCMS (m/z): 492.2 (MH+); LC R, = 2.68 min.

The synthetic route of 486424-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS VACCINES AND DIAGNOSTICS, INC.; WO2008/106692; (2008); 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. 951626-95-2, name is Ethyl 4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., name: Ethyl 4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

[00593] A 60 % dispersion of sodium hydride in mineral oil (0.395 g, 9.88 mmol) was added to a stirred solution of ethyl 4-oxo-4,5,6,7-tetrahydropyrazolo[l,5-a]pyrazine-2- carboxylate (1.88 g, 8.98 mmol) in DMF at 0 C. The mixture was stirred at this temperature for 1 h. Then, benzyl bromide was added and the mixture was stirred at room temperature for further 3 h. The mixture was diluted with water and extracted with DCM. The organic layer was separated, dried (Na2S04), filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 20/80). The desired fractions were collected and the solvents evaporated in vacuo to yield ethyl 5 oenzyl- 4-oxo-4,5,6,7-tetrahydropyrazolo[l,5-a]pyrazine-2-carboxylate as a white oil (1.87 g, 66 % 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; VANDERBILT UNIVERSITY; CONN, P., Jeffrey; LINDSLEY, Craig, W.; STAUFFER, Shaun, R.; BARTOLOME-NEBREDA, Jose Manuel; CONDE-CEIDE, Susana; MACDONALD, Gregor, James; TONG, Han Min; ALCAZAR-VACA, Manuel Jesus; ANDRES-GIL, Jose Ignacio; WO2013/192350; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1458-18-0, The chemical industry reduces the impact on the environment during synthesis 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

Production Example 18-1 Methyl 3-amino-5,6-dimethylpyrazine-2-carboxylate A mixture of methyl 3-amino-5,6-dichloro-2-pyrazine carboxylate (200 mg, 0.90 mmol), X-Phos (170 mg, 0.36 mmol), tris(dibenzylideneacetone)dipalladium(0) (82 mg, 0.090 mmol), tetramethyltin (0.31 mL, 2.3 mmol), and N-methylpyrrolidinone (2 mL) was stirred at 130 C. for 2 hours under microwave irradiation. The reaction mixture was cooled to room temperature, water was added thereto at the same temperature, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate_heptane=3:2) to obtain the title compound (80 mg, 49% yield). 1H-NMR Spectrum (400 MHz, CDCl3) delta (ppm): 2.44 (s, 3H), 2.46 (s, 3H), 3.97 (s, 3H), 6.22 (br s, 2H).

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, Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Lt.d; Tanaka, Keigo; Fukuyama, Takashi; Murai, Norio; Itano, Wataru; Hirota, Shinsuke; Iida, Daisuke; Azuma, Hiroshi; (32 pag.)US2016/168176; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1379338-74-5,Some common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, molecular formula is C7H3Cl2N3, 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.

Intermediate 22: 1 ,1-Dimethylethyl (2/~)-2-{r(7-chloropyridor3,4-6lpyrazin-5- yl)amino1methylV4-morpholinecarboxylate; 1 , 1-dimethylethyl (2f~)-2-(aminomethyl)-4-morpholinecarboxylate (for preparation see: J. Medicinal Chemistry, 2009, 52 (15), 4810-4819) (6g, 27.7mmol) was dissolved in N-methyl-2-pyrrolidinone (NMP) (60ml_) and to this was added DIPEA (7.27ml_, 41.6mmol) and 5,7-dichloropyrido[3,4-b]pyrazine (5.55g, 27.7mmol). This was split between 4 large microwave vials and each was heated at 130C for 30min. They were monitored by LCMS and were given a further 10min at 130C. The reaction mixtures were partitioned between ethyl acetate (700ml) and diluted aqueous ammonium chloride (1 litre). The aqueous was reextracted with ethyl acetate (300ml) and the combined organics were washed with aqueous ammonium chloride (500ml), dried over sodium sulfate and concentrated in vacuo to yield a crude brown oil. It was dissolved in DCM and passed through silica (70g) eluting with DCM (6 X 40ml) then 5% ethyl acetate in DCM (2 X 40ml), 10% ethyl acetate in DCM (5 X 40ml) then 15% ethyl acetate in DCM (2 X 40ml) then 20%ethyl acetate in DCM (2 X 40ml). Appropriate fractions were combined and concentrated in vacuo to yield: N8231-100-2, orange-yellow slightly gummy solid, 7.7gLCMS (Method B): Rt = 1.17min, MH+ 380

The synthetic route of 1379338-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; ATKINSON, Stephen John; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander G; SHIPLEY, Tracy Jane; WILSON, David Matthew; WATSON, Robert J; WO2012/123312; (2012); 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 951626-95-2 as follows. Product Details of 951626-95-2

A solution of lithium hydroxide monohydrate (2.73 g, 65.0 mmol) in H20 (30.0 mL) was added to a suspension of ethyl 4-oxo-4,5 ,6,7-tetrahydropyrazolo [1,5 -a]pyrazine-2- carboxylate (2.72 g, 13.0 mmol) in THF (30 mL) and MeOH (30 mL) at 0 C. Then, the suspension was stirred at rt overnight. The solvents were removed. H20 (20 mL) wasadded. The clear solution was cooled to 0 C, conc. HC1 (5.42 mL, 65.0 mmol) was added to bring pH to 3. The suspension was stirred at 0 C for 2 h, filtered, and dried to give a white solid (2.2 g, 93%). LC-MS(ESI) m/z: 182.1 [M+H].

According to the analysis of related databases, 951626-95-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 24241-18-7, These common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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.

[0953] To a solution of3,5-dibromopyrazin-2-amine (234g, 932 mmol) in DCM (700 mL) and titanium (IV) chloride(174 g, 926 mmol), tert-butyl nitrite (572 g, 5.55 mol) wasslowly added. The resulting mixture was stirred for 2 h atroom temperature and treated with water (500 mL). Theresulting mixture was extracted with DCM (3×500 mL). Thecombined organic layers were concentrated under reducedpressure. The resultant residue was purified by flash colunmchromatography on silica gel (EtOAc/petroleum ether (1:50v/v)) to obtain compound 90d as colorless oil (210 g, 83%yield). Mass Spectrum (LCMS, ESI pos.): Calcd. forC4 HBr2ClN2 : 272.8 (M+H). found 272.6.

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, NV; Player, Mark R.; Meegalla, Sanath K.; Illig, Carl R.; Chen, Jinsheng; Wilson, Kenneth J.; Lee, Yu-Kai; Parks, Daniel J.; Huang, Hui; Patel, Sharmila; Lu, Tianbao; US2014/364414; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, 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 76537-18-3, name: 3-Bromo-5-chloropyrazin-2-amine

A flask was charged with 3-bromo-5-chloropyrazin-2-amine (0.24 g, 1.2 mmol, D-L Chiral Chemicals), 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.24 g, 1.2 mmol, Aldrich), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.041 g, 0.058 mmol), and cesium fluoride (0.53 g, 3.5 mmol). tert-Butyl alcohol (6.1 mL) and water (1.6 mL) were added, and the mixture was degassed and heated to 60 C. for 1.5 hours, then at 70 C. overnight, then at 100 C. for 1.5 hours. Upon cooling, the reaction mixture was partitioned between water and EtOAc, and the layers were separated. The aqueous layer was extracted with two additional portions of EtOAc and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The product was purified by flash chromatography, eluting with a gradient of 0-10% MeOH in DCM to afford a pale yellow solid (0.14 g, 58%). LCMS for C8H9ClN5 (M+H)+: calculated m/z=210.1; found 210.1.

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, 3-Bromo-5-chloropyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

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