Category: 54013-06-8

Electric Literature of 54013-06-8, 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. 54013-06-8, name is Ethyl 5-aminopyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Example 3 5-{[(6-Bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}pyrazine-2-carboxylic acid (0773) (0774) 100 mg (0.26 mmol) of the compound from example 2A and 43 mg (0.26 mmol) of 377 ethyl 5-aminopyrazine-2-carboxylate were dissolved in 2 ml of 49 DMF. 72 mg (0.64 mmol) of 153 potassium tert-butoxide were added in portions to the solution. The reaction mixture was stirred at RT overnight, and then 1.3 ml (1.3 mmol) of 1 M 196 sodium hydroxide solution were added. After stirring at 80 C. for 1 h and cooling to RT, the mixture was adjusted to pH 1-2 with 1 M hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic phase was removed and washed with saturated sodium chloride solution. After the organic phase had been dried over sodium sulfate and the solvent had been removed on a rotary evaporator, the residue was taken up in a little DMF and purified by means of preparative HPLC (method 6). After the solvent-water mixture had been removed, the residue was taken up in a little acetonitrile, water was added and then the mixture was lyophilized. Since solvent residues were still present, the lyophilizate was redissolved in 124 dichloromethane and 61 ethyl acetate, 43 water was added again and the mixture was lyophilized again. The resulting lyophilizate was redissolved once again in dichloromethane and 378 tert-butanol, water was added and the mixture was lyophilized again. The lyophilizate thus obtained was dried at 100 C. under high vacuum for a total 9 h. In this way, 39 mg (29% of theory, 90% purity) of the 379 title compound were obtained. (0775) 1H-NMR (600 MHz, DMSO-d6): delta [ppm]=13.54 (br. s, 1H), 12.03 (s, 1H), 9.71 (s, 1H), 9.01 (s, 1H), 8.10 (d, 1H), 8.04 (d, 1H), 7.93 (dd, 1H), 7.66-7.60 (m, 2H), 7.58-7.50 (m, 3H), 2.41 (s, 3H). (0776) LC/MS (Method 1, ESIpos): Rt=0.96 min, m/z=463/465 [M+H]+.

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

Reference:
Patent; Bayer Pharma Aktiengesekkschaft; BECK, Hartmut; THALER, Tobias; KAST, Raimund; MEIBOM, Daniel; MEININGHAUS, Mark; TERJUNG, Carsten; DELBECK, Martina; LUSTIG, Klemens; MUENSTER, Uwe; OLENIK, Britta; (100 pag.)US2017/260140; (2017); 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. 54013-06-8, name is Ethyl 5-aminopyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H9N3O2

Intermediate Example lnt-5: Ethyl 2-(4-{1-[(ferf-butoxycarbonyl)amino]cyclobutyl}phenyl)-3-phenyl- imidazo[1,2-a]pyrazine-6-carboxylate To a mixture of crude fert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)- carbamate [lnt-1-A] (213 mg, 0.38 mmol, 1.0 eq), ethyl 5-aminopyrazine-2- carboxylate (CAS-Nr. 54013-06-8, 70.5 mg, 0.42 mmol, 1.1 eq.) and diisopropylethylamine (0.055 ml_, 0.42 mmol, 1.1 eq) in 2.3 ml_ butyronitrile was added pre- dried 3A mol sieves. The mixture was heated overnight at 120. The reaction mixture was partitioned between DCM/water and was filtered through a phase separator. The remaining volatile organic components were removed by the use of a rotary evaporator. In parallel we conducted the same experiment in the absence of diisopropylethylamine following the same protocol. The crude materials of both experiments were combined and purified via MPLC (Biotage Isolera, 25 g Snap- cartridge; eluent: hexane/ethyl acetate (1/1) -> ethyl acetate) to deliver 69 mg (14%, yield based on combined amount of fert-butyl (1-{4-[bromo(phenyl)acetyl]- phenyl}cyclobutyl)carbamate) of the title compound. UPLC-MS (Method 1): RT = 1.43 min; m/z = 513 (M+H) +.

The synthetic route of 54013-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SCOTT, William; HAeGEBARTH, Andrea; INCE, Stuart; REHWINKEL, Hartmut; POLITZ, Oliver; NEUHAUS, Roland; BOeMER, Ulf; WO2013/104610; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

54013-06-8, name is Ethyl 5-aminopyrazine-2-carboxylate, 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. SDS of cas: 54013-06-8

Chloroacetaldehyde (9.5 mL of a 50 wt% solution in water) was added to a mixture of aminopyrazine (2.00 g, 12.0 mmol), sodium bicarbonate (2.00 g, 23.8 mmol) and absolute ethanol (100 mL). The reaction was heated to 90 C for 16 hours. After cooling to room temperature, the reaction was concentrated and purified by flash chromatography (silica, 0-10% methanol/chloroform) to give pure 1-1 as a tan colored solid. 1 H NMR (400 MHz, CDCI3) delta 9.18 (s, 1 H), 9.01 (d, J= 1.4, 1 H), 7.93 (d, J= 1 .1 , 1 H), 7.84 (s, 1 H), 4.51 (q, J= 7.1 , 3H), 1 .46 (t, J = 7.1 , 4H).

The synthetic route of 54013-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; NOVARTIS AG; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; PARASELLI, Prasuna; LEONG, Seh Yong; ROLAND, Jason Thomas; MISHRA, Pranab Kumar; YEUNG, Bryan KS; ZOU, Bin; WO2014/78813; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 54013-06-8,Some common heterocyclic compound, 54013-06-8, name is Ethyl 5-aminopyrazine-2-carboxylate, molecular formula is C7H9N3O2, 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.

Step 1: Ethyl 5-amino-6-bromopyrazine-2-carboxylate: To a solution of ethyl 5-aminopyrazine-2-carboxylate (880 mg, 5.26 mmol) in acetonitrile (20 mL) at RT was added NBS (984 mg, 5.53 mmol), the resultant solution was stirred at RT for 1 hour. The reaction mixture was diluted with EtOAc, washed with sat NaHCO3, brine and water, dried, filtered, and concentrated to afford the crude product, which was purified by ISCO 24 g silica gel column, 0 to 50% EtOAc in Heptane, 30 min). 1.01 g, 78% yield. LC-MS (m/z): 247.9 (MH+), 0.51 min.

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

Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 54013-06-8, 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. 54013-06-8, name is Ethyl 5-aminopyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Example 5: Ethyl 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2- a razine-6-carboxylate To a mixture of crude fert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)- carbamate [lnt-1-A] (245 mg, 0.44 mmol, 1.0 eq) and ethyl 5-aminopyrazine-2- carboxylate (CAS-Nr. 54013-06-8, 81.1 mg, 0.49 mmol, 1.1 eq.) in 2.7 mL bu- tyronitrile was heated at 120 for 1.5h. A substan tial amount of the deprotected free amine was detected by UPLC analysis. For isolation, the volatile components were removed using a rotary evaporator and the resulting crude material was purified via MPLC [Biotage Isolera, 25 g Snap-cartridge; eluent: DCM -> DCM/ethanol (95/5)] to deliver 38 mg (21 %) of the title compound. UPLC-MS (Method 1): RT = 0.90 min; m/z = 414 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 1.26 (t, 3H), 1.60 (m, 1 H), 1.88-2.07 (m, 3H), 2.12 (s br, 2H), 2.26-2.37 (m, 2H), 4.30 (q, 2H), 7.39 (d, 2H), 7.57(d, 4H), 7.60-7.68 (m, 3H).

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

Adding a certain compound to certain chemical reactions, such as: 54013-06-8, name is Ethyl 5-aminopyrazine-2-carboxylate, 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 54013-06-8, name: Ethyl 5-aminopyrazine-2-carboxylate

A mixture of aminopyrazine, 3-bromo-1,1,1-trifluoropropan-2-one and ethanol was heated in a microwave synthesizer at 180 C for 60 minutes. After cooling to room temperature, the solvent is removed and the dark brown residue is purified by flash chlromatography (silica, 30-60% ethyl acetate/hexanes) to give I-3 as a tan colored solid. 1H NMR (400 MHz, CDCI3) delta 9.24 (s, 1H), 8.99 (d, J= 1.4, 1H), 8.10 (s, 1H), 4.51 (q, J= 7.1, 2H), 1.46 (t, J= 7.1, 3H).

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; IRM LLC; NOVARTIS AG; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; PARASELLI, Prasuna; LEONG, Seh Yong; ROLAND, Jason Thomas; MISHRA, Pranab Kumar; YEUNG, Bryan KS; ZOU, Bin; WO2014/78813; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem