Month: September 2021

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

Adding a certain compound to certain chemical reactions, such as: 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, 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 143591-61-1, Formula: C6H3BrClN3

To a solution of compound 2 (example 1, step 2) (80 mg, 0,28 mmoi) in THE (5 mL) was added NaH (22 mg, 0.56 mmoi, 60 wt% in oil) at RI. The mixture was stirred at RT for 30 minutes, then the product from step 1 (81 rng, 0.35 mmoi) was added. The mixture was heated to 60C for 3 hours. After cooling to RT, the mixture was poured into water (5 mL) and extracted with EtOAc (5 niL x 3). The combined organic layer was washed with brine, driedover MgSO4, filtered and concentrated in vacuo. The residue was purified by Prep.?FIPLC to afford the title compound (70 mg) as a white solid. LRMS mz (M+H) 482.1, 484.1 found, 482.1,484.1

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, 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 110223-15-9, name is 2-Amino-3-benzyloxypyrazine, 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 110223-15-9, Computed Properties of C11H11N3O

General procedure: For aromatic urea derivatives; the appropriate aromatic isocyanate(3.0 mmol) was added to a solution of the appropriate 2-amino-3-benzyloxy pyrazine derivative (2.5 mmol) in THF(10 mL). The reaction was refluxed for 3e6 h. After cooling, thereaction mixture was evaporated and the residue was purified byprecipitation in cold methanol and filtered to give the targetcompound(s). For aliphatic urea derivatives; the appropriatealiphatic isocyanate derivative (1.02 mmol) was added to a solutionof the appropriate 2-amino-3-benzyloxy pyrazine derivative(0.85 mmol) in dry THF (5 mL) in the presence of NaH (60% inmineral oil, 68 mg, 1.71 mmol). The reaction was refluxed for 5 h.After cooling, the reaction mixture was evaporated and the residuewas purified by flash column chromatography (SiO2, EA/n-Hex 1/4).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-3-benzyloxypyrazine, and friends who are interested can also refer to it.

Reference:
Article; Elkamhawy, Ahmed; Park, Jung-eun; Hassan, Ahmed H.E.; Pae, Ae Nim; Lee, Jiyoun; Paik, Sora; Park, Beoung-Geon; Roh, Eun Joo; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 268 – 278;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6966-01-4,Some common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, 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 methyl 3-amino-6-bromopyrazine-2-carboxylate (100 mg, 0.43 mmol) in MeOH (5 mL) was added 2 mL of NaOH aqueous solution (5 N). After being stirred at 50C for 4 h, the mixture was cooled and acidified with 1 M HCl to a pH of 2. The precipitate was collected by filtration and washed with water to afford the product of 3-amino-6- bromopyrazine-2-carboxylic acid (90 mg, yield: 96%). XH-NMR (DMSO-ifc, 400 MHz) delta 8.38 (s, 1H), 7.51-7.56 (m, 2H). MS (M+H)+: 218 / 220.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-6-bromopyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1379338-74-5, 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. 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

A solution of tert-butyl 3-(aminomethyl)-5-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate (4.74 g, 13.7 mmol), 5,7-dichloropyrido[4,3-b]pyrazine (2.75 g, 13.7 mmol) and DIPEA (2.12 g, 16.4 mmol) in THF (20 mL) was stirred at room temperature for 48 hours. The volatiles were removed under reduced pressure and the residue was treated with ethyl acetate, washed with brine, dried over Na2SO4, filtered, and concentrated to give the title compound.

The chemical industry reduces the impact on the environment during synthesis 5,7-Dichloropyrido[3,4-b]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; Su, Wei-Guo; Deng, Wei; Ji, Jianguo; US2014/121200; (2014); 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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine

5-Bromo-lH-pyrrolo [2,3-b] pyrazine (59.4 g & ‘ 0.3 was added in the reactor Methyl-N-(1-(4-methylpiperazin-1-yl) -2,3-dihydro-1 // – Inden-5-yl) -benzamide(112 mg, 0.3 Mmol), bistriphenylphosphine dioxane 1 E (22 mg & ‘ 0.03 mmol), tricyclic Hexylphosphine (16 mg, 0.06 mmol), cuprous iodide carbonate (99 mg, 0 3 mmol), 6 drops of N, N-diisopropyl Ethylamine was added, and at the end of reaction Kh ‘at 80 C, ethyl acetate and aqueous ammonia were added And washed with saturated NaCl solution, dried over anhydrous Na2S04, filtered, Dried, and purified by column chromatography to give the title compound

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

Reference:
Patent; NANJING SHENGHE PHARMACEUTICAL CO., LTD.; WANG, YONG; ZHAO, LIWEN; LIU, YANG; ZHANG, JINGZHONG; WANG, DEZHONG; GAO, YIPING; CHEN, HONGYAN; ZHANG, CANG; ZHANG, DI; (68 pag.)TWI523856; (2016); B;,
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. 1422772-78-8, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1422772-78-8

Step 5. Methyl 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylate. To a 0 C. suspension of 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (145 g, 602 mmol) in MeOH (1.5 L) was added dropwise SOCl2 (93 g, 781 mmol) over a period of 40 min. after the addition, the resulting mixture was heated to reflux for 4 hours, which time suspended solution became clear and then yellow solid was precipitated. TLC (petroleum ether/EtOAc, 1:1) showed starting material was consumed completely. The reaction mixture was evaporated to dryness, which was triturated with MTBE to give methyl 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylate (109 g, 71%) as a yellow solid.

According to the analysis of related databases, 1422772-78-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Thorarensen, Atli; Brown, Matthew Frank; Casimiro-Garcia, Agustin; Che, Ye; Coe, Jotham Wadsworth; Flanagan, Mark Edward; Gilbert, Adam Matthew; Hayward, Matthew Merrill; Langille, Jonathan David; Montgomery, Justin Ian; Telliez, Jean-Baptiste; Unwalla, Rayomand Jal; US2015/158864; (2015); 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. 4430-75-5, name is Octahydro-2H-pyrido[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. category: Pyrazines

To a solution of octahydropyrido[1,2-a]pyrazine (50 mg, 0.38 mmol) and NEt3 (83 muL, 0.59 mmol) in DCM (15 mL) at 0 C. was added a suspension of 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene-9-sulfonyl chloride from Example 121 (93 mg, 0.12 mmol) in DCM (5 mL) and the resulting mixture warmed to RT after 10 min then stirred for 1 h. The reaction mixture was diluted with DCM, washed with a saturated aqueous NaHCO3 solution then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-8% MeOH in EtOAc) then freeze-dried from MeCN/H2O affording 132 (36 mg, 62%) as a white solid. LCMS: RT 2.90 min [M+H]+ 498.3. 1H NMR (DMSO, 400 MHz): delta 8.78 (1H, d, J=2.41 Hz), 8.01 (1H, s), 7.94 (1H, s), 7.63 (1H, dd, J=8.63, 2.42 Hz), 7.28 (1H, d, J=8.62 Hz), 5.73-5.72 (1H, m), 4.63-4.59 (4H, m), 3.53 (1H, d, J=11.02 Hz), 3.43 (1H, d, J=9.07 Hz), 2.70-2.68 (2H, m), 2.33-2.32 (1H, m), 2.19-2.11 (1H, m), 1.93-1.92 (3H, m), 1.62 (1H, d, J=12.59 Hz), 1.57-1.52 (2H, m), 1.49 (6H, t, J=6.30 Hz), 1.38-1.16 (2H, m), 1.01-0.87 (1H, m)

The synthetic route of 4430-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; US2012/245144; (2012); 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. 22047-25-2, name is Acetylpyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Acetylpyrazine

Hydrobromic acid (33 wt% in AcOH, 3.1 mL, 17.1 mmol, 1.05 equiv) and bromine (0.85 mL, 16.5 mmol, 1.0 equiv) were sequentially, slowly added to a solution of 2-acetylpyrazine (2.0 g, 16.4 mmol, 1.0 equiv) in glacial acetic acid (18 mL) and the reaction was stirred for 4 h at 23 C. The yellow solid was collected, washed with glacial acetic acid (7 mL) and dried to afford crude 2-(2-bromo)acetylpyrazine hydrobromide 88b (3.3 g, 71% crude) as a colorless solid, which was used without further purification. To a solution of 2-(2-bromo)acetylpyrazine hydrobromide 88b prepared above (1.0 g, 3.55 mmol, 1.0 equiv) in 95% EtOH was added thiourea (0.33 g, 4.3 mmol, 1.2 equiv) and DIPEA (1.8 mL, 10.3 mmol, 2.9 equiv) and the brown suspension was heated at reflux for 3 h. After cooling to rt the solvent was evaporated and the residue washed with CH2Cl2. The solid was dried under reduced pressure to afford the title compound (0.60 g, 95%) as a yellow solid: Rf = 0.27 (9:1 CH2Cl2-MeOH); 1H NMR (600 MHz, CD3OD) delta 7.32 (s, 1H), 8.40 (d, J = 2.3 Hz, 1H), 8.51 (s, 1H), 9.01 (d, J = 1.2 Hz, 1H); 13C NMR (150 MHz, CD3OD) delta 109.5, 142.5, 143.0, 144.6, 147.5, 148.6, 170.4; HRMS (APCI+) calcd for C7H7N4S [M+H]+ 179.0386, found 179.0382 (error 2.2 ppm).

The synthetic route of 22047-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Meissner, Anja; Boshoff, Helena I.; Vasan, Mahalakshmi; Duckworth, Benjamin P.; Barry III, Clifton E.; Aldrich, Courtney C.; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6385 – 6397;,
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. 768-05-8, name is Pyrazinoic acid hydrazide, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H6N4O

General procedure: 2.3. General procedure for the synthesis of N’-(2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)pyrazine-2-carbohydrazide(8-14)The quest for the synthesis of N’-(2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)pyrazine-2-carbohydrazide (8-14) wasaccomplished in two steps as outlined in Scheme 1. A mixture of2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-one (1-7) (1 mmol),commercially available pyrazine-2-carbohydrazide (PZH)(1.5 mmol) in methanol and chloroform mixture (1:1 v/v), andcatalytic amount of acetic acid (0.1 mL) was added and refluxed for2-3 h. On the completion of reaction, a solid mass was formed.After cooling to room temperature, the precipitate was filtered offand washed with cold mixture of ethanol and water. The crude product was recrystallized from ethanol [16].

According to the analysis of related databases, 768-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mangalam; Sebastian Antony Selvan; Sankar; Journal of Molecular Structure; vol. 1129; (2017); p. 305 – 312;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem