Tag: M.W=200-300

Reference of 41270-66-0, 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. 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Add 2-butanone (1440 ml) to the reaction flask,Sodium iodide (134.87g, 2.5 eq),2-chloro-5,6,-diphenylpyrazine (96 g, 1.0 eq),Nitrogen protection. Concentrated sulfuric acid (14.41 g, 0.4 eq) was added dropwise at room temperature. After the addition is completed, the temperature is raised toThe reaction was refluxed for 6 hours. After the reaction is completed,The reaction solution was concentrated to dryness. Add water (960ml),Dichloromethane (960 ml), liquid. The organic phase was concentrated to dryness filter,The solid is dried under reduced pressure,2-iodo-5,6,-diphenylpyrazine (88 g), yield 68.2%

The synthetic route of 5-Chloro-2,3-diphenylpyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Kesheng Pharmaceutical Research And Development Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Liu Huixin; Shen Junhui; Zhang Jicheng; Huang Luning; Tao Anping; An Jianguo; Chen Qian; Gu Hong; (10 pag.)CN109384734; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1260812-97-2, 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. 1260812-97-2, name is 2-Bromo-3-methyl-5H-pyrrolo[2,3-b]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To anydrous ethanol (60 mL) were added2-bromo-3-methyl-5H-pyrrolo[2,3-b]pyrazine (6.00 g, 28 mmol), ammonium formate (27.00 g,428 mmol) and 10% Pd/C (6 g). The mixture was refluxed for 5 hours under nitrogen protection.The reaction mixture was filtered through a celite pad, concentrated in vacuo to remove thesolvent, and the residue was purified by silica gel column chromatography (PE/EA (v/v) =411-211) to give the title compound as a yellow solid (3.10 g, 82 %).MS (ESI, pos. ion) m/z: 134.2 [M+Ht.

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-Bromo-3-methyl-5H-pyrrolo[2,3-b]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (303 pag.)WO2018/108125; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 1458-01-1, A common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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 solution of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (1.2 g, 5.92 mmol, 1.00 equiv) and 2-bromo-1,1-dimethoxyethane (2 g, 11.83 mmol, 2.00 equiv) in acetonitrile (20 mL) wasirradiated with microwave for 40 mm at 120 ¡ãC. After completion the resulting solution was concentrated under vacuum and the residue was purified by a silica gel column eluting with dichloromethane/methanol (10:1) to give the title compound (300 mg, 22percent) as a yellow solid. LC-MS (ES, mlz): 227 [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; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); 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. 173253-42-4, name is 2-Amino-5-bromo-6-chloropyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 173253-42-4

General procedure: To the DMF (1ml) was added dropwise phenyl chloroformate (2equiv). The mixture was stirred for 5min at room temperature. Then 6-chloro-2-aminopyrazine (1mmol) was introduced to the mixture. After 5min, the solvent (isopropyl alcohol:diethyl ether, v/v=1:2) was poured into the mixture. The precipitated product 6a was filtered off, washed with the solvent and dried.

The synthetic route of 173253-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kwak, Se Hun; Gong, Young-Dae; Tetrahedron; vol. 69; 34; (2013); p. 7107 – 7111;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 944709-42-6, name is 6,8-Dibromo-[1,2,4]triazolo[1,5-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. Quality Control of 6,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine

A flask equipped with a mechanical stirrer was charged with 6,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (63.9 g, 230 mmol) and DMF (700 mL) followed by(1r,4r)-4-(4-amino-1H-pyrazol-1-yl)cyclohexanol (41.7 g, 230 mmol) and N-ethyl-N-isopropylpropan-2-amine (80 mL, 460 mmol). The reaction mixture was stirred at ambient temperaturefor 16 h. The reaction mixture was diluted with water (1.5 L) and filtered. The collectedsolid was triturated with water to give the title compound (84.0 g, 97percent); MS m/z: 378,380 (M+H)+; 1H NMR (400 MHz, DMSO-d6) delta 10.63 (s, 1H), 8.54 (d, J = 5.6 Hz, 1H), 8.07 (s, 1H),7.76 (s, 1H), 4.61 (d, J = 4.3 Hz, 1H), 4.20¡À4.05 (m, 1H), 3.48 (dq, J = 10.7, 5.6, 5.1 Hz, 1H),2.08¡À1.85 (m, 4H), 1.85¡À1.64 (m, 2H), 1.43¡À1.19 (m, 2H).

The synthetic route of 6,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Article; George, Dawn M.; Huntley, Raymond J.; Cusack, Kevin; Duignan, David B.; Hoemann, Michael; Loud, Jacqueline; Mario, Regina; Melim, Terry; Mullen, Kelly; Somal, Gagandeep; Wang, Lu; Edmunds, Jeremy J.; PLoS ONE; vol. 13; 9; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, 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 87486-34-8, category: Pyrazines

Example 112 CGI PHARM6 0WO5-Bromo-l-methyl-3-(pyridin-3-ylamino)pyrazin-2(lH)-one 112a112aA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was charged with THF (15 mL), 3,5-dibromo-l-methylpyrazin- 2(lH)-one (1.00 g, 3.73 mmol), 3-aminopyridine (351 mg, 3.73 mmol) and sodium tert- butoxide (789 mg, 8.21 mmol). After bubbling nitrogen through the resulting solution for 30 min, Pd2Br2(t-Bu3P)2 (29 mg, 0.037 mmol) was added, and the reaction mixture was stirred at room temperature for 2.5 h. After this time the reaction was partitioned between ethyl acetate (50 mL) and water (50 mL) and filtered. The aqueous layer was separated and extracted with ethyl acetate (2 x 25 mL). The organic layers were combined, washed with brine (50 mL) and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford a 35percent yield (370 mg) of 112a as a brown solid: mp >250¡ãC; ]H NMR (500 MHz, DMSO- 6) delta 9.75 (s, 1H), 9.08 (d, 1H, / = 2.5 Hz), 8.32 (m, 1H), 8.24 (dd, 1H, / = 5.0, 1.5 Hz), 7.40 (s, 1H), 7.36 (dd, 1H, J = 8.5, 4.5 Hz), 3.45 (s, 3H); MS (APCI+) m/z 281.0 (M+H).

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; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; CURRIE, Kevin S.; WANG, Xiaojing; YOUNG, Wendy B.; WO2012/31004; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 622392-04-5,Some common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, molecular formula is C4H2BrIN2, 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-5-iodopyrazine (284.9 mg, 1 mmol), lH-imidazole (64.7 mg, 0.95 mmol), toluene (10 mL), and K2CO3 (345.5 mg, 2.5 mmol), Cul (19.0 mg, 0.1 mmol), trans-N,N’- dimethylcyclohexane-l, 2-diamine (0.032 mL, 0.2 mmol) were heated at 100 C overnight. The reaction mixture was then partitioned between H20 and ethyl acetate. The organic layer was dried over MgSCL, filtered, and concentrated under vacuum. Purification by silica gel chromatography (ethyl acetate in hexane, 0-100%), yielded 2-(lH-imidazol-l-yl)-5-iodopyrazine (219.7 mg, 85%) as an off-white solid which contains a small amount of inseparable byproduct 2-(lH-imidazol-l- yl)-5-bromopyrazine. LC-MS 273.1 [M+H]+, RT 0.74 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-iodopyrazine, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; CHEN, Guangming; BHATTACHARYYA, Anuradha; JIANG, Yao; KARP, Gary, Mitchell; NARASIMHAN, Jana; TURPOFF, Anthony; ZHANG, Nanjing; (0 pag.)WO2020/5882; (2020); 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. 446286-94-8, name is 5-Bromo-N,N-dimethylpyrazin-2-amine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H8BrN3

EXAMPLE 2 P N-(4-(5-(dimethylamino) pyrazin-2-ylsulfonyl) benzyl) imidazo [1, 2-al pyridine-6-carboxamidea. N-f4-f5-fdimethylamino)pyrazin-2-ylsulfonyl)benzyl) acetamide:The mixture of XANTPHOS (0.573 g, 0.990 mmol), Cs2C03 (6.45 g, 19.80 mmol), Pd2(dba)3 (0.453 g, 0.495 mmol),4-(acetamidomethyl)benzenesulfinic acid, sodium salt (3.51 g, 14.85 mmol), 5-bromo-N,N-dimethylpyrazin-2-amine (2 g, 9.90 mmol) in Toluene (50 ml) was degassed and heated to 120 C for overnight. Cooled to RT, added EtOAc, washed with water, dried and concentrated, The Biotage purification afforded 1.6g of the target compound (48%).1HNMPv (CDC13): delta 8.75(s, 1H). 8.03 (s, 1H), 7.87 (d, 2H), 7.38 (d, 2H), 6.11 (b, 1H), 4.45 (d, 2H), 3.21 (s, 6H), 2.16 (s, 3H).

The synthetic route of 446286-94-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GENENTECH, INC.; BAIR, Kenneth, W.; BAUMEISTER, Timm; BUCKMELTER, Alexandre, J.; CLODFELTER, Karl, H.; DRAGOVICH, Peter; GOSSELIN, Francis; HAN, Bingsong; LIN, Jian; REYNOLDS, Dominic J.; ROTH, Bruce; SMITH, Chase, C.; WANG, Zhongguo; YUEN, Po-Wai; ZHENG, Xiaozhang; WO2012/31197; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, 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: C4H3BrClN3

3-Bromo-5-chloropyrazin-2-amine (200 mg, 0.96 mmol), triethylamine (290 mg, 2.88 mmol), cuprous iodide (5 mg, 0.33 mmol) and bis(triphenyl) Palladium dichloride (13 mg, 0.02 mmol) was dissolved in tetrahydrofuran (5 mL).The reaction solution was stirred at room temperature.Then, trimethylethynyl silicon (0.15 mL, 1.06 mmol) was slowly added dropwise to the above reaction solution.After the completion of the dropwise addition, the obtained reaction liquid was transferred to a condition of 55 C to continue the reaction for 1 hour. After the reaction system is cooled to room temperature,The reaction solution was diluted with ethyl acetate (50 mL) and filtered.The filtrate was concentrated under reduced pressure.The residue obtained was subjected to silica gel column chromatography(PE/EA(nu/nu) = 30/1) purified,The title compound was obtained as a pale yellow solid (208 mg,96%).

The synthetic route of 76537-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Wang Yejun; Yi Kai; Lei Yibo; Zhang Yingjun; S ¡¤geerdeman; Yan Huan; Nie Biao; Xu Juan; Chen Jianping; Chen Yunfu; Zhang Weihong; Cheng Lijun; Ye Weiliang; (197 pag.)CN110117285; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 1196151-53-7, name is 6-Bromopyrazine-2-carboxylic acid, molecular formula is C5H3BrN2O2, 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: C5H3BrN2O2

Example 21 Preparation of Compound 297 Step A-Synthesis of Intermediate Compound Int-21a A mixture of 6-bromopyrazine-2-carboxylic acid (404 mg, 1.99 mmol), 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (1 g, 1.99 mmol), 2M sodium carbonate (4 ml, 8 mmol), Bis(triphenylphosphine)palladium(II) dichloride (70 mg, 0.1 mmol) was suspended in DME (7 ml), DMf (2 ml), water (3 ml) and EtOH (2 ml) in a sealed tube and heated in a microwave oven at 120 C. for 20 min. Then concentrated under vacuum, applied onto Prep HPLC and eluted with H2O (0.1% TFA) and Acetonitrile (0.1% TFA). This resulted in 0.96 g (95%) of 6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)pyrazine-2-carboxylic acid as a white solid. LC-MS (ES, m/z) C23H19FN4O6S: 498. Found: 499 [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 1196151-53-7, its application will become more common.

Reference:
Patent; McComas, Casey Cameron; Liverton, Nigel J.; Habermann, Joerg; Koch, Uwe; Narjes, Frank; Li, Peng; Peng, Xuanjia; Soll, Richard; Wu, Hao; Palani, Anandan; Dai, Xing; Liu, Hong; He, Shuwen; Lai, Zhong; Dang, Qun; Zorn, Nicolas; US2014/199263; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem