Month: February 2021

Related Products of 1159811-97-8, A common heterocyclic compound, 1159811-97-8, name is 6-Bromo-2-methylimidazo[1,2-a]pyrazine, molecular formula is C7H6BrN3, 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.

Into a 1-neck round-bottom flask N,N-diisopropylamine (0.50 mL, 3.6 mmol) was dissolved in tetrahydrofuran (4.0 mL) and cooled at -78 C. 1.6 M n-butyllithium in hexane (1.9 mL, 3.1 mmol) was added. The reaction was stirred at -78 C. for 30 min and 6-bromo-2-methylimidazo[1,2-a]pyrazine (from Ark Pharm, 0.500 g, 2.36 mmol) in tetrahydrofuran (6.0 mL) was added dropwise. The reaction mixture was stirred at -78 C. for 45 min and hexachloroethane (0.72 g, 3.1 mmol) was added. The resulting mixture was stirred at -78 C. for 1 h. The reaction was quenched with NH4Cl solution and then partitioned between EtOAc and water. The EtOAc extract was washed with brine, dried (MgSO4), and stripped in vacuo. The residue was chromatographed on silica gel eluting with 40% EtOAc in hexanes to give the desired product (0.25 g, 43%). LCMS calculated for C7H6BrClN3 (M+H)+: m/z=245.9. Found: 245.9. 1H NMR (CDCl3, 400 MHz) delta 8.72 (1H, s), 7.68 (1H, s), 2.56 (3H, s) ppm.

The synthetic route of 1159811-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Li, Yun-Long; Zhu, Wenyu; Mei, Song; Glenn, Joseph; US2014/121198; (2014); 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 33332-25-1

Preparation 10 To a solution of methyl 5-chloropyrazine-2-carboxylate (500 mg) in MeOH (5 mL) was added 28% NH3 aqueous solution (5 mL), and the mixture was stirred at ambient temperature. The precipitated solid was collected by filtration and washed with diisopropyl ether to afford 5-chloropyrazine-2-carboxamide (303 mg) as a solid.

The synthetic route of 33332-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; EP2123651; (2009); 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. 22047-25-2, name is Acetylpyrazine, A new synthetic method of this compound is introduced below., Formula: C6H6N2O

General procedure: Almac CRED (200 mg) and NADP or NAD (10 mg)were charged into a 100 mL round bottomed flask and dissolvedin 0.1 M potassium phosphate buffer (pH 7, ca. 50 mL). Next, IPA(7 mL) was added, followed by a solution of ketone (900-1700 mg) in DMSO (2.5-5 mL, depending on solubility). This was shaken at room temperature overnight and the reaction progresswas checked by 1H NMR. If not complete, additional CRED (100-200 mg) and NADP or NAD (10 mg) were added and shaking wascontinued. This was repeated until the reaction reached completion.If the reaction appeared to stall or proceed very slowly, experimentalmethod C was used.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Rowan, Andrew S.; Moody, Thomas S.; Howard, Roger M.; Underwood, Toby J.; Miskelly, Iain R.; He, Yanan; Wang, Bo; Tetrahedron Asymmetry; vol. 24; 21-22; (2013); p. 1369 – 1381;,
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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 5-chloropyrazine-2-carboxylate

Diisobutylaluminium hydride (1.0 M in toluene; 6.4 mL, 6.40 mmol) was added dropwise to a cooled solution of methyl 5-chloropyrazine-2-carboxylate (690 mg, 4.00 mmol) in THF (13.6 mL) at -55 C. The reaction was stirred under these conditions for 1 hour and then quenched by addition of saturated aqueous NH4C1 (25 mL) and EtOAc (25 mL). An emulsion formed and 2N aqueous HC1 was added to clear the emulsion (5 mL). The layers were separated, and the aqueous layer was extracted with EtOAc. The organic layerwas washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in heptane. Product fractions were evaporated to dryness to afford 5-chloropyrazine-2-carbaldehyde (385 mg, 68%) as a beige solid. ?H NMR (500 MHz, CDC13, 27 C) 8.75 (1H, d), 8.96 (1H, d), 10.15 (1H, d).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ASTRAZENECA AB; SCOTT, James, Stewart; MOSS, Thomas, Andrew; YANG, Bin; VARNES, Jeffrey, Gilbert; O’DONOVAN, Daniel, Hillebrand; NISSINK, Johannes, Wilhelmus, Maria; HUGHES, Samantha, Jayne; BARLAAM, Bernard, Christophe; WU, Dedong; BROO, Dan, Anders; (224 pag.)WO2018/19793; (2018); 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. 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 3,6-dibromopyrazine-2-carboxylate

Step 1. Synthesis of Compound (B) as Described in the General Reaction Scheme; 3,6-dibromo-pyrazine-2-carboxylic Acid LiOH (655 mg, 27 mmol) is added to a solution of 3,6-dibromo-pyrazine-2-carboxylic acid methyl ester (A) (J. Med. Chem. 1969, 12, 285-87) (2.7 g, 9 mmol) in THF:water:MeOH (18:4.5:4.5 mL). The reaction is stirred at 5 C. for 30 min, concentrated in vacuo, taken up in DCM and washed with 1N HCl. The organic phase is dried over anhydrous MgSO4 and concentrated in vacuo to afford compound (B). 1H NMR (250 MHz, CDCl3) delta (ppm) 8.70 (s, 1H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Andrews, Martin James Inglis; Chambers, Mark Stuart; Van De Poel, Herve; Bar, Gregory Louis Joseph; US2009/286798; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 27825-21-4, name is Methyl 3-chloropyrazine-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 27825-21-4, Application In Synthesis of Methyl 3-chloropyrazine-2-carboxylate

A mixture of 1 (504?mg, 2.9?mmol) and O-benzylhydroxylamine (1073?mg, 8.72?mmol) in diisopropylethylamine (1.44?mL, 8.72?mmol) was irradiated in microwave at 100?C for 1?h. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography using ethyl acetate and petroleum ether (1:4) as an eluent to provide 2 as a yellow solid in 16% yield, mp: 60-62?C. 1H NMR (400?MHz, DMSO-d6) delta 10.33 (s, 1H, N-H), 8.50 (d, J?=?2.3?Hz, 1H, pyrazine-H), 8.13 (d, J?=?2.3?Hz, 1H, pyrazine-H), 7.47 (dd, J?=?8.2, 1.6?Hz, 2H, Ph-H), 7.42-7.33 (m, 3H, Ph-H), 4.96 (s, 2H, CH2), 3.82 (s, 3H, CH3). 13C NMR (100?MHz, DMSO-d6) delta 165.51, 155.09, 146.75, 136.19, 134.63, 128.69 (2?xC), 128.30 (2?xC), 128.18, 125.53, 76.85, 52.44. ESI-MS: m/z 260.3 (M+1), 282.4 (M+23). C13H13N3O3 [259.3].

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

Reference:
Article; Sun, Lin; Gao, Ping; Dong, Guanyu; Zhang, Xujie; Cheng, Xiqiang; Ding, Xiao; Wang, Xueshun; Daelemans, Dirk; De Clercq, Erik; Pannecouque, Christophe; Menendez-Arias, Luis; Zhan, Peng; Liu, Xinyong; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 714 – 724;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 313340-08-8, These common heterocyclic compound, 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, 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.

Compound D1Sa (30 mg, 0.137 mmol), B3Rb (41 mg, 0.137 mmol) and DIPEA (35 mg, 0.274 mmol) were dissolved in 1,4-dioxane (2 mL), the reaction solution was heated to 130 C. and stirred for 16 hours in seal. The LCMS indicated the reaction was complete, the reaction mixture was concentrated in vacuo, the residue was purified via preparative TLC (DCM/MeOH=15:1) to afford compound D6Rb (30 mg, yield 45%) as a pale yellow solid. MS m/z 486.2 [M+H]+, 488.2 [M+H]+.

The synthetic route of 313340-08-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hangzhou Innogate Pharma Co., Ltd.; ZHANG, Hancheng; LIU, Shifeng; YE, Xiangyang; (92 pag.)US2019/308993; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-29-5, 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. 33332-29-5, name is 2-Amino-5-chloropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

2-(6-Chloro-5-cyano-pyridin-3-yl)-pentanoic acid (5-chloro-pyrazin-2-yl)-amide The title product was synthesized following the general procedure E2 starting from 2-(6-Chloro-5-cyano-pyridin-3-yl)-pentanoic acid and 5-Chloro-pyrazin-2-ylamine, (0.10 g, 53%). 1H NMR (400 MHz, Chloroform-d3) delta 9.30 (s, 1H), 8.56 (d, J = 2.3 Hz, 1H), 8.27 (s, 1H), 8.18 (d, J= 2.3 Hz, 1H), 7.92 (s, 1H), 3.59 (t, J= 7.6 Hz, 1H), 2.27 – 2.12 (m, 1H), 1.90-1.80 (m, 1H), 1.46 – 1.19 (m, 2H), 0.98 (t, J= 7.3 Hz, 3H). C15H13N5OCl2, Calculated [350.20], found [M+H+], 2Cl pattern 350-352, RT=1.60 (method f).

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, 2-Amino-5-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Siena Biotech S.p.A.; Caramelli, Chiara; Federico, Cesare; Gabellieri, Emanuele; Magnani, Matteo; Micco, Iolanda; EP2878339; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 123-32-0, 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. 123-32-0, name is 2,5-Dimethylpyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Preparation of 3,6-dimethyl-2- (2-furoyl) pyrazine, comprising the steps of:(1) 2,5-dimethyl pyrazine take 0.2mmol, 2- furylcarboxamido acid 0.4mmol, 0.02 mmol silver phosphate, potassium persulfate 0.4mmol 5mL reaction tube was placed in dichloromethane was added 1.4mL , 0.6 mL of distilled water was added, and the reaction mixture was placed in a 5mL tube and placed in an oil bath at 40 heated, reaction 24h, cooled to room temperature to obtain a reaction solution;(2) The step (1) the resulting reaction mixture was directly concentrated to give a concentrate, the concentrate with ethyl acetate / petroleum ether = 1/2 (v / v) as the developing solvent, separation by thin layer chromatography to give 11mg target The product, 27% yield.

The chemical industry reduces the impact on the environment during synthesis 2,5-Dimethylpyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Henan Agricultural University; Wu Zhiyong; Zhao Mingqin; Li Yuan; (10 pag.)CN108101856; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 36070-80-1, 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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The corresponding substituted salicylanilide 2 (1 mmol) and 5-chloropyrazine-2-carboxylic acid 1 (1 mmol) were dissolved in dryDMF (8 mL), the solution was cooled to 10 C and DCC (1.2 mmol)was added in three portions during 1 h. The mixture was stirred foradditional 3 h at the same temperature and then stored at 4 C for20 h. The precipitate of N,N0-dicyclohexylurea was removed byfiltration and the solvent was evaporated in vacuo till dryness. Thecrude products 3 were purified by one or repeated crystallizationfrom ethyl acetateehexane mixture. 4.1.4.1 4-Chloro-2-{[4-(trifluoromethyl)phenyl]carbamoyl}phenyl 5-chloropyrazine-2-carboxylate (3a) White solid; yield: 35%; mp: 163.4-165.0 C. IR (ATR): 3372 (NH), 3081, 2934, 2857, 1751 (C=O ester), 1663, 1648, 1633, 1600, 1530, 1520, 1477, 1411, 1323, 1297, 1274, 1259, 1190, 1163, 1125, 1104, 1066, 1020, 879, 839, 826, 786, 715, 702, 668. 1H NMR (500 MHz, DMSO-d6): delta 9.40 (1H, bs, NH), 9.23 (1H, d, J = 1.4 Hz, H3″), 8.69 (1H, d, J = 1.4 Hz, H5″), 8.13 (1H, d, J = 2.6 Hz, H3), 7.78 (2H, d, J = 8.4 Hz, H3′, H5′), 7.61 (2H, d, J = 8.3 Hz, H2′, H6′), 7.57 (1H, dd, J = 2.5 Hz, J = 8.6 Hz, H5), 7.52 (1H, d, J = 8.7 Hz, H6); 13C NMR (126 MHz, CDCl3): delta 161.43, 160.35, 154.25, 146.70, 146.04, 144.31, 140.76, 139.71, 132.72, 131.40, 127.46, 126.66 (q, J = 32.8 Hz), 126.19 (q, J = 3.8 Hz), 123.93 (q, J = 272.6 Hz), 123.92, 120.45. MSmonoisotopic (calc/meas): 455.0/455.2; Anal. Calcd. for C19H10ClF3N3O3 (456.20): C, 50.02; H, 2.21; N, 9.21; Found: C, 50.34; H, 2.45; N, 9.43.

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, 5-Chloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Baranyai, Zsuzsa; Kratky, Martin; Vin?ova, Jarmila; Szabo, Nora; Senoner, Zsuzsanna; Horvati, Kata; Stola?ikova, Ji?ina; David, Sandor; Bosze, Szilvia; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 692 – 704;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem