Month: August 2021

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

Synthetic Route of 1458-01-1, 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. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Intermediate A.13,5-Diamino-6-chloropyrazine-2-carboxylic acidA mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 I) and NaOH (6 mol/l in water; 240 ml; 1 .44 mol) is refluxed for 3 h. The mixture is allowed to cool to r.t. and then neutralized by addition of hydrochloric acid (6 mol/l in water; approx. 240 ml_). Water (200 ml) is added. The precipitate formed is filtered off with suction, washed with water and dried at 60°C.C5H5CIN402 ESI Mass spectrum: m/z = 189 [M+H]+; m/z = 187 [M-H]-

The synthetic route of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; KLEY, Joerg; FRATTINI, Sara; HAMPRECHT, Dieter; HECKEL, Armin; WO2015/7516; (2015); A1;,
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

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

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

These common heterocyclic compound, 1422772-78-8, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-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. Formula: C7H4BrN3O2

To a suspension of 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (Example 83 Step 1, 145 g, 602 mmol) in MeOH (1.5 L) at 0C was added thionyl chloride (93 g, 781 mmol) dropwise over 40 minutes. The reaction was heated to reflux for 4 hours before cooling and concentrating in vacuo. The resulting solid was triturated with TBME to afford the title compound as a yellow solid (109 g, 71%) that was taken directly on to the next step.

The synthetic route of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; THORARENSEN, Atli; BROWN, Matthew Frank; CASIMIRO-GARCIA, Agustin; CHE, Ye; FLANAGAN, Mark Edward; GILBERT, Adam Matthew; HAYWARD, Matthew Merrill; TELLIEZ, Jean-Baptiste; UNWALLA, Rayomand Jal; TRUJILLO, John I.; LIANG, Sidney Xi; (212 pag.)WO2016/178110; (2016); 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

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

Electric Literature of 4774-14-5, These common heterocyclic compound, 4774-14-5, name is 2,6-Dichloropyrazine, 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.

To a solution of tert-butyl azetidin-3-ylcarbamate hydrochloride (LXIII) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture was added 2,6-dichloropyrazine (LXIV) (1.428 g, 9.58 mmol) and the reaction was stirred at 95C for 3 h. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous Na2504, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes-*hexanes:EtOAc 1:1) to yield tert-butyl (1-(6- chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXV) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C12H17C1N402 mlz 285.1 (M+H).

The synthetic route of 4774-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (271 pag.)WO2017/24026; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 5900-13-0, 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 5900-13-0 as follows.

General procedure: Toa solution of 5-bromo-3-methoxypyrazin-2-amine (500 mg, 2.45 mmol) in pyridine(5 mL) at room temperature was added 3-chlorophenyl)methanesulfonyl chloride(552 mg, 2.45 mol) over 5 min. The mixture was stirred 10 mins, the pyridineevaporated, then DCM (60 mL) and water (10 mL) was added. The phases wereseparated and the organic phase was washed with brine (5 mL), dried (Na2SC>4),the mixture filtered and the filtrate evaporated to dryness to afford an orangeoil which was chromatographed on silica (Heptane: EtOAc 1 :1) to afford thetitle compound as a light brown solid (483 mg, 48%); The procedure to prepare N-(5-bromo-3-methoxypyrazin-2-yl)-1-(3-chlorophenyl)- methanesulfonamide was used except that methyl 3 -(chlorosulfonyl)benzoate was substituted for 3-chlorophenyl)methanesulfonyl chloride. In addition, the reaction was carned out at 60C rather than at room temperature (15%); mlz=40 1.9, 403.9 (MH).

According to the analysis of related databases, 5900-13-0, the application of this compound in the production field has become more and more popular.

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