Tag: M.W=200-300

Synthetic Route of 486424-37-7, The chemical industry reduces the impact on the environment during synthesis 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life.

Step 1: 3-Amino-6-bromo-N-methoxy-N-methyl pyrazi ne-2-carboxamideTo a stirred suspension of 3-amino-6-bromopyrazine-2-carboxylic acid (45 g, 206 mmol) andO,N-dimethylhydroxylamine hydrochloride (20.13 g, 206 mmol) in DMF (295 mL) at RT wasadded triethylamine (115 mL, 826 mmol) under N2 supply. The resulting mixture was cooledto 0C and to this yellow suspension T3P (50 % in EtOAc) (151 g, 237 mmol) was added dropwise over 5 mm (keeping T below 10C – exotherm). The mixture was allowed to warm to RT and stirred for 2-3 hours. During the reaction the contents had set solid into a gel. The flask was diluted with a further 200 ml of DMF and was warmed to 40 C and was leftovernight. Further triethylamine (50 mL, 0.4 equiv), O,N-dimethylhydroxylamine hydrochloride (10 g, 0.5 equiv) and T3P (80 g, 0.5 equiv) were added and the reaction mixture was warmed to 4000 and was allowed to stir for 2-3 hours. The mixture was allowed to cool to RT and then stirred for three days. The mixture was worked up by the addition of 2M HCI (100 mL) and was diluted with ethyl acetate (1 L) and water (500 mL). The biphasic mixture was separated. The aqueous layer was basified with 2M NaOH (- 150 mL), organicextract was added back and the biphasic mixture was shaken. The organic was extracted, washed with brine, dried over MgSO4, filtered and dried under vacuum to give a yellow oil. The crude yellow oil was loaded directly onto a 750 g column (in DCM 20 mL) and was eluted with iso-Hex / EtOAc (0- 70 % gradient). The fractions containing pure product were combined and evaporated to give a yellow oil. Diethyl ether (50 mL) was added and this wasevaporated under vacuum to give a pale yellow solid;LC-MS: Rt 0.88 mins; MS m/z 263.1 MH+; Method 2minLC_v003

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-Amino-6-bromopyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; (395 pag.)WO2015/162459; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 24241-18-7, 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.

To an aqueous (10 kg) solution of 3,5-dibromopyrazine-2-amine (1018 g, 4.03 mol), 2-bromo-1,1-dimethoxyethane (1.79 kg, 4.14 mol) was added at room temperature and stirred for 2 hours while heating under reflux. To the reaction solution, water (15.3 kg) and sodium hydrogen carbonate (744 g) were added and further stirred for 15 minutes. The resultant solid substance was obtained by filtration to obtain the titled compound (1106 g, 3.99 mmol, 99%) as a brown solid substance.1H-NMR (400 MHz, DMSO-d6) delta 7.90 (s, 1H), 8.23 (s, 1H), 9.02 (s, 1H).

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; Oncotherapy Science, Inc.; US2012/59162; (2012); 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. 1159811-97-8, name is 6-Bromo-2-methylimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., name: 6-Bromo-2-methylimidazo[1,2-a]pyrazine

To a well stirred solution of 6-bromo-2-methyl imidazo[1,2-a]pyrazine (3 g, 14.15 mmol) in DMF (15 ml) was added N-lodoosuccinimide (3.82g, 16.98 mmol) and the reaction mixture was allowed to stir at 80C for 12 h under nitrogen. After complete consumption of the SM (Monitored by LCMS) the reaction mixture was diluted with ethyl acetate, washed successively with water and brine, dried over sodium sulphate and evaporated under reduced pressure to get the crude compound, which was purified by column chromatography (100-200 mesh silica gel, eluent; 20% ethyl acetate in hexane) to give the title compound as a yellowish solid [1.5 g, 31% (After two steps)]. LCMS rt 2.89 min MH* 338.1H NMR (400 MHz, DMSO-de) delta 8.74 (s, 1H), 8.49 (s, 1H), 2.44 (s, 3 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; SALVENSIS; GARDNER, John Mark Francis; BELL, Andrew Simon; (78 pag.)WO2018/130853; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. category: Pyrazines

Example 30 Preparation of 6-bromo-N-(4-(4-(oxetan-3-yl)piperazin-l-yl)phenyl)imidazo[l,2- a]pyrazin-8-amine [0268] To 4-(4-(oxetan-3-yl)piperazin-l-yl)aniline (2.00 g, 8.57 mmoles), hunig’s base (3.29 mL) and 6,8-dibromoimidazo[l,2-a]pyrazine (2.37 g, 8.57 mmoles) was added in dimethylformamide (43 mL). The reaction was stirred at 85C in a pressure tube for overnight. The material was quenched with saturated sodium bicarbonate, extracted with methylene chloride (120 mL x 3), the organic layers were combined and washed with water (120 mL x 3), dried over anhydrous sodium carbonate and concentrated. The crude material was purified using a 120 g Isco column and eluted off using a stepwise gradient of 0-60% (10% methanol / methylene chloride). The desired fractions were combined and concentrated to provide the title compound as a light yellow solid.

The synthetic route of 63744-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD CONNECTICUT, INC.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; HALCOMB, Randall; KROPF, Jeffrey, E.; LEE, Seung, H.; LI, Jiayao; LO, Jennifer, R.; MITCHELL, Scott, A.; SCHMITT, Aaron; WU, Qiaoyin; XIONG, Jin-min; XU, Jianjun; ZHAO, Zhongdong; CHANDRASEKHAR, Jayaraman; LANSDON, Eric; WO2013/188856; (2013); 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.

To a stirred solution of methyl 3-amino-5, 6-dichloropyrazine-2-carboxylate (500 mg, 2.25 mol, 1 equiv) and 2- (tributylstannyl) -1, 3-oxazole (806.5 mg, 2.25 mol, 1.00 equiv) in 1, 4-dioxane (20 mL) were added LiCl (190.9 mg, 4.50 nMol, 2 equiv) , tricyclohexylphosphane (126.3 mg, 0.45 nMol, 0.2 equiv) and Pd 2 (dba) 3. CHCl 3 (466.2 mg, 0.45 nMol, 0.20 equiv) in portions at room temperature under nitrogen atmosphere. The resulted mixture was stirred for 4h at 140 under nitrogen atmosphere with microwave irritation. The resulted mixture was concentrated under reduced pressure. The residue was purified by Prep-TLC (CH 2Cl 2 /MeOH 20: 1) to afford methyl 3-amino-6-chloro-5- (1, 3-oxazol-2-yl) pyrazine-2-carboxylate (160 mg, 27.9%) as a yellow solid. LCMS: m/z (ESI) , [M+H] + = 255.1.

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

Application of 1208082-91-0, 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. 1208082-91-0, name is 6,8-Dibromo-2-methylimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 1-05 (0.62 g, 2.13 mmol) was dissolved inCHC1 (4 mE) and N-bromosuccinimide (455 mg, 2.56mmol) was added. The reaction mixture was heated under microwave irradiation at 120 C. for 1 h. On cooling, the mixture was adsorbed in silica and purified by l3iotage column chromatography (DCMJMeOH from 100% to 95:5) to give intermediate 1-06 (720 mg, Y: 91%) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 6,8-Dibromo-2-methylimidazo[1,2-a]pyrazine. I believe this compound will play a more active role in future production and life.

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

Related Products of 6966-01-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(Step 6-ii) To a solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (1 g, 4.33 mmol) in 10 mL THF was added a solution of LiOH (540 mg, 12.86 mmol) in 20 mL of water. The mixture was stirred at room temperature for 4 hours and acidified with 6M HCl to a pH of 2. The yellow precipitate was collected by filtration and washed with water. After drying in vacuo, the product, 3-amino-6-bromopyrazine-2-carboxylic acid (600 mg, 2.75 mmol, 64% yield), can be used directly in the next reaction without further purification.

The synthetic route of Methyl 3-amino-6-bromopyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/36272; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1215852-11-1, A common heterocyclic compound, 1215852-11-1, name is 7-tert-Butyl 3-ethyl 5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-3,7(8H)-dicarboxylate, molecular formula is C13H20N4O4, 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.

A flask was charged with 7-(t-butyl) 3-ethyl 5,6-dihydro-[l,2,4]triazolo[4,3-a]pyrazine- 3,7(8H)-dicarboxylate (3.00 g, 10.1 mmol, 1.00 equiv), Li OH (1.21 g, 30.3 mmol, 3.00 equiv), EtOH (20 mL) and water (2 mL). The resulting solution was stirred for 2 h at room temperature and concentrated under reduced pressure to provide 2.70 g (crude) of 7-(t-butoxycarbonyl)- 5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyrazine-3-carboxylic acid. LCMS (ESI, m/z): 269 [M+H]+

The synthetic route of 1215852-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; WEBER, Olivia D.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; JONES, Todd K.; (275 pag.)WO2019/46318; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, 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 221136-66-9, Computed Properties of C9H11BrN2O3

Example 8 r3-(2,2-Difluoro-2-phenyl-ethylamino)-6-methyl-2-oxo-2H-pyrazin-1-vn- acetic acid ethyl ester(3-Bromo-6-methyl-2-oxo-2H-pyrazin-1 -yl)-acetic acid ethyl ester was reacted with 2,2-difluoro-2-phenyl-ethylamine in the presence of a base, at elevated temperature, to yield the title compound as shown in the Scheme above. Table 5 below lists the reagent amounts, base and temperature combinations applied to this reaction, as well as yield.

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; JANSSEN PHARMACEUTICA, N.V.; WO2007/146553; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

622392-04-5, name is 2-Bromo-5-iodopyrazine, 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: 2-Bromo-5-iodopyrazine

Preparation of compound 22a: 2-(2,2-difluoroethoxy)-5-iodopyrazineTo a solution of 2,2-difluoroethanol (0.74 g, 8.7 mmol) in THF (5OmL) at room temperature was added sodium butoxide (1.13 g, 11.4 mmol) and stirred for 15 min. The reaction mixture was cooled to 0 0C and a solution of 2-bromo-5-iodopyrazine (2.5 g, 8.7 mmol) in THF (50 ml_) was added slowly over 5 min. The reaction mixture was allowed to warm to room temperature and stirred for 16 h. The mixture was diluted with ethyl acetate and washed with sat. NH4CI. The organic layer was dried over MgSO4, filtered and concentrated which gave the title compound 22a (2.3 g, 90%).

The synthetic route of 622392-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; NINKOVIC, Sacha; BRAGANZA, John Frederick; COLLINS, Michael Raymond; KATH, John Charles; LI, Hui; RICHTER, Daniel Tyler; WO2010/16005; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem