Author: Jessica.F

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. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 68774-77-6

A mixture of 8-chloro-[l,2,4]triazolo[4,3-a]pyrazine (620 mg, 4.0 mmol) and (S)-tert-butyl pyrrolidin-3-ylcarbamate (1.2 g, 6.5 mmol) in diethylisopropyl amine (3 mL) was heated to 120 C. for 2 h. After cooling to room temperature, the mixture was diluted with 10% MeOH in EtOAc and washed with saturated aqueous solutions of KH2PO4 and NaHCO3, followed by brine. The organic layerwas concentrated in vacuo and the residue purified by flashchromatography (SiO2, 2 to 5% MeOH in CH2Cl2 as eluent) to give the desired compound as a foam (1.15 g, 95% yield, which was used directly for the next step). MS: (ES) m/z305.2 (M+H+).

According to the analysis of related databases, 68774-77-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (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. 4858-85-9, name is 2,3-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H2Cl2N2

2,3-Dichloropyrazine (III-9) (500 mg, 3.36 mmol) and 4-chlorophenol (II-17) (431 mg, 3.36 mmol) were dissolvedin DMF (10 mL), potassium carbonate (557 mg, 4.03 mmol) was added and the mixture was stirred at 90C for 15 hr.The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layerwas washed successively with water and saturated brine, and the solvent was evaporated under reduced pressure. Theresidue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 100:0 ? 85:15) to give compound(IV-102) (yield 809 mg, quantitative) as a white solid

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 4858-85-9.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; WATANABE, Atsushi; SATO, Yuuki; OGURA, Keiji; TATSUMI, Yoshiyuki; (331 pag.)EP3351533; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 72788-94-4,Some common heterocyclic compound, 72788-94-4, name is 2-Chloro-5-(hydroxymethyl)pyrazine, molecular formula is C5H5ClN2O, 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 Intermediate 112A (2.00 g, 13.84 mmol) in CHCl3 (20 mL) was added active manganese dioxide (4.81 g, 55.3 mmol) and the resulting suspension was refluxed for 2 h. The reaction mixture was cooled to ambient temperature, filtered through Celite and washed with CHCl3 (200 mL). The combined filtrates were washed with brine (200 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Redisep-24 g, 20-30 % EtOAc/ n-hexane) to obtain Intermediate 112B (1.00 g, 50.70%) as a white solid.1H NMR (400 MHz, DMSO-d6) delta ppm 8.98 (d, J = 1.51 Hz, 1 H), 9.04 (d, J = 1.51 Hz, 1 H), 10.07 (s, 1 H). LCMS: The compound did not ionize well.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (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. 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

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. 6270-63-9, name is Pyrazin-2(1H)-one, A new synthetic method of this compound is introduced below., name: Pyrazin-2(1H)-one

Weigh the pyrazin-2(1H)-one (481 mg, 5 mmol) in a 50 mL single-mouth bottle. Add anhydrous N,N-dimethylformamide (6 mL), Sodium hydride (240 mg, 6 mmol, 60%) was added and the mixture was stirred at room temperature. Weighed after 20 minutes Ethyl 2-bromoacetate (1.0 g, 10.0 mmol, Dissolved in 4 mL of anhydrous N,N-dimethylformamide) and added dropwise to the reaction flask. After the addition was completed, the reaction was stirred at room temperature overnight. Stop the reaction, The reaction was quenched by dropwise addition of water (2 mL). Add water (30mL), Extracted with ethyl acetate (30 mL ¡Á 3), Combine the organic phase to concentrate, The residue was purified by column chromatography ( petroleum ether / ethyl acetate (v / v) = 1 / 1) The title compound was obtained as a pale yellow liquid (360 mg, 40%).

The synthetic route of 6270-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Xu Tengfei; Jin Chuanfei; Zhong Wenhe; Xue Yaping; (45 pag.)CN109761892; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 69816-35-9, These common heterocyclic compound, 69816-35-9, name is 6-(Trifluoromethyl)pyrazin-2-amine, 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.

1-(2-Chlorobenzoyl)-3-(6-trifluoromethyl-2-pyrazinyl)urea, having a melting point of about 179-180 C., from 1.5 g. of 2-amino-6-trifluoromethylpyrazine and 1.6 g. of 2-chlorobenzoylisocyanate.

Statistics shows that 6-(Trifluoromethyl)pyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 69816-35-9.

Reference:
Patent; Eli Lilly and Company; US4293552; (1981); A;,
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

Application 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.

Intermediate b (5.0 g, 0.034 mol) was added to triethyl orthoformate (50 mL), and the reaction was carried out at 80 C. The reaction time was monitored with a plate. The reaction liquid was directly filtered with cold suction, and the filter cake was washed with petroleum ether. After the cake was dried, 4.8 g of a yellow powder was obtained with a yield of 90.1%.

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

Reference:
Patent; Jiangxi Science and Technology Normal University; Zhu Wufu; Zheng Pengwu; Xu Shan; Liu Xiaobo; Zhang Qian; Zhou Lingjia; Han Haoyun; Yu Li; Zhou Hualan; Qiu Yufeng; (25 pag.)CN110467616; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 113305-94-5, 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.

A solution of tert-butyl 4-((2-chloro-5-iodopyridin-4-ylamino)methyl)piperidine-1- carboxyiate (Synthesis 170-B) (0.100 g, 0.22 mmol), dichlorobis(triphenyiphosphine)- palladium (II) (0.009 g, 0.01 mmol), trimethyl(2-methylbut-3-yn-2-yloxy)silane (0.048 mL, 0.24 mmol) and copper iodide (0.002 g, 0.01 mmol) was heated under microwave irradiation for 5 min at 120 0C. The crude mixture was concentrated in vacuo and filtered through a pad of silica, eluting with hexane / ethyl acetate (8 / 2), to give the crude product which was used without further purification. The crude pyridine (0.085 g, 0.163 mmol), 2-amino-4-cyanopyrazine (0.023 g, 0.195 mmol), Xantphos (0.015 g, 0.026 mmol), cesium carbonate (0.106 g, 0.326 mmol), dichlorobis(triphenylphosphine)- palladium (II) (0.012 g, 0.013 mmol) in dioxane (1.2 mL) were stirred at room temperature under nitrogen for 10 min, then heated under microwave irradiation for 60 min at 150 CC. The reaction mixture was purified by ion exchange on SCX-II acidic resin (2 g), eluting with methanol / dichloromethane (1 / 1 ), then 2M ammonia-methanol. The basic fractions were combined and solvent was removed in vacuo. The crude product was purified by preparative thin layer chromatography, eluting with methanol / dichloromethane (1 / 19), to give the title compound as a yellow solid (0.024 g, 27%).1H NMR (CDCI3, 500 MHz) delta 8.62 (s, 1 H), 8.44 (s, 1 H), 8.00 (s, 1 H), 7.17 (s, 1 H), 5.19 (t, 1 H, J = 5.8 Hz) 4.19-4.16 (m, 2H), 3.17 (t, 2H, J = 6.1 Hz), 2.72 (t, 2H, J = 11.3 Hz), 1.84- 1.75 (m, 3H), 1.66 (s, 6H), 1.47 (s, 9H), 1.27-1.21 (m, 2H), 0.90-0.84 (m, 1 H). LCMS (4) Rt = 2.17 min; m/z (ESI+) 492 [MH+].

Statistics shows that 5-Aminopyrazine-2-carbonitrile is playing an increasingly important role. we look forward to future research findings about 113305-94-5.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 25911-65-3,Some common heterocyclic compound, 25911-65-3, name is 3-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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.

d) 4-Amino-2-[(2,2,2-trifluoroethoxy)methyl]pteridine Obtained using the procedure described in section c of Example 2, starting with 7.2 g (0.060 mole) of 3-amino-2-pyrazinecarbonitrile and 14.2 g (0.091 mole) of 2-(2,2,2-trifluoroethoxy)acetamidine in 230 ml of absolute ethanol. Refluxing time: 7 hours. Yld: 6.5 g (42%), m.p. 145-147 C. (ethyl acetate). NMR (DMSO-d6): delta=4.2 (2H, q); 4.6 (2H, s); 8.3 (2H, peak exchangeable with CF3 COOD); 8.7 (1H, m); 9.0 (1H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Aminopyrazine-2-carbonitrile, its application will become more common.

Reference:
Patent; Lipha, Lyonnaise Industrielle Pharmaceutique; US5167949; (1992); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem