Tag: M.W=100-200

91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, 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. HPLC of Formula: C6H9N3

5,6,7,8-Tetrahydroimidazo[1 ,2-a]pyrazine(l17) (4.53 g, 36.8 mmol) and triethylamine (6.16 mL, 44.2 mmol) were dissolved in dichloromethane (DCM) (200 mL) and treated with di-tert-butyl dicarbonate (10.25 mL, 44.2 mmol). The solution was stirred at RT for 48 h and concentrated in vacuo to afford a crude oil. The crude product was purified by flash chromatography (Isolera, 340 g, 0-100% 2M ammonia in methanokdichloromethane (1 :9)/dichloromethane) to afford 3 fractions. Fraction 2 was identified by LC/MS as containing desired product. The residue was dissolved in ethyl acetate (300 ml), washed with saturated sodium bicarbonate solution (50 ml_), water (2 x 50 ml_), brine (50 ml_), dried over anhydrous sodium sulfate and concentrated to afford product in 6.77g. LC/MS = 224 (M+H)+, retention time = 0.71 minutes (2 minute method (high pH)).

The synthetic route of 91476-80-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALL, Ian David; WALTER, Daryl Simon; WO2010/125101; (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. 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Safety of 5-Chloropyrazine-2-carbonitrile

To a solution of rac-(2S,3R,4R)- I -acetyl-4-amino-N,2,3-trimethyl- 1,2 ,3,4-tetrahydroqu inoline-6- carboxamide (for a preparation, see Intermediate 189, 37 mg, 0.134 mmol) in NMP (1 mL) was added 5-chloropyrazine-2-carbonitrile (37.5 mg, 0.269 mmol), and DIPEA (0.070 mL, 0.403 mmol) and the resultant solution heated to 150 C for 30 mm by microwave irradiation. The reaction mixture was directly purified by MDAP (Formic) to afford the desired product as a yellow solid (11mg). LCMS (2 mm Formic): Rt = 0.69 mi [M-Hf = 377.

The synthetic route of 36070-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

Intermediate 13-2: 6-chloropyrazine-2-carboxamideA solution of 6-chloro-pyrazine carboxylic acid (2.0O g, 12.62 mmol) in DMF (7 mL) was cooled to -40 0C. NMP (2.77 mL, 25.23 mmol) and isobutyl chloroformate 3.27 mL, 25.23 mmol) were added. The temperature was allowed to increase to -20 0C during 20 min and then NH4OH was added. A precipitate was rapidly formed and after 15 min it was filtered off and washed with water. Crystallization from EtOH gave the title compound (670 mg, 34 %) as light-brown needles.1H NMR (500 MHz, DMSO) delta 7.93 (br s, IH), 8.24 (br s, IH), 8.99 (s, IH), 9.12 (s, IH).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 23688-89-3.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/81195; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 63286-28-2,Some common heterocyclic compound, 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, molecular formula is C4H5ClN4, 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.

Compound 49A is added to trimethyl orthoformate,The temperature was raised to reflux for 10 hours, cooled to room temperature, and filtered.Obtaining Compound 49B Solid(2 g, yield 70%).

The synthetic route of 63286-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Chen Huanming; Liang Bo; Zhao Zhongqiang; Cao Wenjie; Xu Wanmei; Li Qingsong; Wang Jianghuai; Zhang Peng; Jiang Zhaojian; Zhang Guiping; Gao Chunhua; Gong Hongju; Zuo Gaolei; (86 pag.)CN108250128; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 54608-52-5, name is 2-Hydrazinopyrazine, 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 54608-52-5, name: 2-Hydrazinopyrazine

A solution of 2-hydrazinopyrazine (1.10 g) in trifluoroacetic anhydride (10 mL) was stirred at room temperature for 4 h. To the mixture was added PPA (12 mL). The reaction mixture was heated at 80 C. for another 15 h. The reaction mixture was cooled to room temperature and filtered to afford the title compound as a white solid (0.94 g, 50.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 189.0 (M+1); 1H NMR (400 MHz, CDCl3) delta: 8.64 (s, 3H).

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Jiancun; Zhang, Yingjun; Zhang, Weihong; Liu, Bing; Zhang, Jiquan; Liu, Jinlei; Zhang, Lu; US2014/228361; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, 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. Recommanded Product: 5-Aminopyrazine-2-carbonitrile

To a suspension of 5-aminopyrazine-2-carbonitrile (750 mg, 6.22 mmol) in THF (10 mL) was added sodium hydride (420 mg, 10.36 mmol) at O5 C. The resulting mixture was then stirred at ambient temperature for 1 h. Compound 305-6 (1.7 g, 5.18 mmol) was added and stirred at 60 C for 4 h. The reaction mixture was quenched with ice-water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (hexanes/ethyl acetate: 5/1) to afford the title compound 306-6 as a yellow solid (1.0 g, 50% yield). LCMS:401.1[M+1]. ?HNIVIR (400 1VIHz, CDC13): 2.34 (s, 3H), 2.36 (s, 3H), 3.46 (s, 3H), 3.81 (s, 3H), 5.16 (s, 2H), 5.69 (s, 1H), 6.46 (s, 1H), 6.63 (s, 1H),8.37 (d, J= 1.2 Hz, 1H), 8.52 (d, J= 1.6 Hz, 1H),14.64 (s, 1H).

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

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, molecular formula is C9H16N2O2, 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. name: (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

To a 500 mL flame dried flask was added (i?)-2-isopropyl-3, 6- dimethoxy-2,5-dihydropyrazine (10.0 g, 54.3 mmol) and anhydrous THF (200 mL). The solution was cooled to -78 °C. “-BuLi (2.5M in hexane, 24.0 mL, 59.7 mmol) was added dropwise. After the solution was allowed to stir at -78 °C for 30 minutes, Compound Int-16b (in 5 mL anhydrous THF) was added dropwise. After the solution was allowed to stir at -78 °C for 1 hour, it was allowed to warm up to room temperature in two hours. Water (100 mL) and Et20 (150 mL) were added. The organic layer was separated and the aqueous layer was extracted with Et20 (100 mL) twice. The organic layers were combined, washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue obtained was purified using Si02 chromatography (40 g, eluted with Et20 in Hexane: 0percent to 3percent) to provide Compound Int-16c (10.43 g, 58.0percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 109838-85-9, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KOZLOWSKI, Joseph A.; ROSENBLUM, Stuart B.; COBURN, Craig A.; SHANKAR, Bandarpalle, B.; ANILKUMAR, G., Nair; CHEN, Lei; DWYER, Michael, P.; JIANG, Yueheng; KEERTIKAR, Kartik, M.; LAVEY, Brian, J.; SELYUTIN, Oleg, B.; TONG, Ling; WONG, Michael; YANG, De-Yi; YU, Wensheng; ZHOU, Guowei; WU, Hao; HU, Bin; ZHONG, Bin; SUN, Fei; JI, Tao; SHEN, Changmao; RIZVI, Razia; ZENG, Qingbei; WO2012/41014; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, 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. HPLC of Formula: C6H4BrN3

To a solution of I-69 (300 mg, 0.6 mmol) in DMF (10 mL) are added I-87 (140 mg, 0.7 mmol), tetrakis(triphenylphosphine)palladium (0) (70 mg, 0.06 mmol) and 2M Na2CO3 (1.5 mL, 3.0 mmol). The mixture is heated to 100 C. for 1 hour in a microwave reactor. The mixture is cooled down and is extracted with H2O (20 mL) and EtOAc (30 mL). The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent to afford the title compound (200 mg). Example 176-180, Table 1-the reaction is run at 120 C.Example 176-180, Table 1-the reaction is run at 120 C. [0509] Example 184-185, Table 1-the reaction is run at 120 C Example 191, Table 1-the reaction is run at 120 C. Example 239-243, Table 1-the reaction is run for 6 hours at 100 C. in an oil bath

The synthetic route of 875781-43-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; BYLOCK, Lars Anders; US2013/195879; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 13924-94-2, 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. 13924-94-2, name is Methyl 5-aminopyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Methyl 5-aminopyrazine-2-carboxylate (8) (0.650g, 4.2483mmol) was reacted with excess of acetic anhydride (5mL) and heated at 90C for 2h. The reaction mixture was evaporated and partitioned between saturated NaHCO3 solution and ethyl acetate. Organic layer was evaporated to get 0.345g of compound 9a as pale yellow solid (yield 41.6%). 1H NMR (400MHz, DMSO-d6) delta 11.29 (s, 1H), 9.41 (d, J=1.4Hz, 1H), 8.96 (d, J=1.4Hz, 1H), 2.18 (s, 3H), 1.81 (s, 3H). C8H9N3O3 [M]: 195.18; MS (ESI) m/z: [M+H]+: 196.05 [M-H]+, 194.05

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 5-aminopyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Trivedi, Prakruti; Adhikari, Nilanjan; Amin, Sk. Abdul; Jha, Tarun; Ghosh, Balaram; European Journal of Pharmaceutical Sciences; vol. 124; (2018); p. 165 – 181;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6164-79-0, 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. 6164-79-0, name is Methyl 2-pyrazinecarboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

[0537] Synthesis of pyrazin-2-ylmethanol: [0538] To a stirred solution of methyl pyrazine-2-carboxylate (0.5 g, 3.62 mmol) in H20 (10 mL) was added NaBH4 (685 g, 18.02 mmol) portion wise at 0 C, and the reaction mixture was allowed to warm to RT and stirred for 30 min under inert atmosphere. To this saturated K2C03 (10 mL) and EtOH (5 mL) was added and stirring was continued for another 1 h at RT. The progress of the reaction was monitored by TLC; the reaction mixture was extracted with EtOAc. The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to afford crude pyrazin-2-ylmethanol (0.3 g). LC-MS: 99.91%; 111.9 (M++l) (column; X-bridge C-18, (50×3.0 mm, 3.5mu); RT 0.72 min. 0.1% TFA in water: ACN; 0.8 ml/min); TLC: 100% EtOAc (Rf: 0.2).

The synthetic route of Methyl 2-pyrazinecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem