Tag: M.W=100-200

Reference of 54608-52-5,Some common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, molecular formula is C4H6N4, 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 sample of 2-hydrazinopyrazine was prepared from 2-chloropyrazine and hydrazineusing a procedure analogous to that described in the literature [P.J. Nelson and K.T. Potts, /. Org. Chem.,27. 3243 (1962)], except that the crude product was extracted into 10% methanol/dichloromethane andfiltered, and the filtrate was concentrated and purified by flash chromatography on silica gel, eluting with100% ethyl acetate followed by 10% methanol in dichloromethane. A mixture of 2-hydrazinopyrazine(820 mg, 7.45 mmol), trifluoroacetic acid (2.55 g, 22.4 mmol), and polyphosphoric acid (10 mL) washeated to 140 C with stirring for 18 h. The solution was added to ice and neutralized by the addition ofammonium hydroxide. The aqueous solution was extracted three times with ethyl acetate, washed withbrine, and dried over anhydrous magnesium sulfate. Concentration followed by flash chromatography(silica gel, 1:1 hexane:ethyl acetate, then 100% ethyl acetate) afforded the title compound as a solid.’H NMR (500 MHz, CDC13): 5 8.17-8.20 (m, 2H), 9.54 (s, 1H); C/MS 189 (M+l).

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/23750; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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 939412-86-9, SDS of cas: 939412-86-9

At 0C To a solution of (3-chloropyrazin-2-yl) methanamine hydrochloride (compound 102) (2.48 g, 13.8 mmol, 1.0 equiv.) In dichloromethane (80 mL) was added triethylamine (5.58 g, 55.2 mmol , 4.0 equivalents) and ((benzyloxy) carbonyl) -L-proline (compound 103) (3.43 g, 13.8 mmol, 1.0 equiv) Stirred at 0 & lt; 0 & gt; C for 15 minutes, A solution of 2- (7-azobenzotriazole) -N, N, N ‘, N’-tetramethyluronium hexafluorophosphate (HATU, 5.50 g, 14.5 mmol, 1.05 equiv) was added and the reaction was allowed to react at 0 C to room temperature for 5 minutes. The reaction solution was diluted with dichloromethane (200 mL), washed successively with ammonium chloride solution (200 mL x 1), saturated sodium bicarbonate solution (200 mL x 1), saturated brine (200 mL x 1), and the organic phase was washed with anhydrous sulfuric acid The sodium was dried, filtered, the filtrate was dry and the residue was purified by column chromatography (eluent: Dichloromethane: methanol = 80: 1) to give benzyl (S) -2 – (((3-chloropyrazin-2-yl) methyl) carbamoyl) pyrrolidine-1-carboxylate (2.85 g , Yield: 55.1%). Light brown oil;

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; Dongguan Zhen Xing Beite Pharmaceutical Co., Ltd.; Cai Xiong; Zhong Xianbin; Ye Chunqiang; He Qijie; Tan Shifeng; Qian Changgeng; (44 pag.)CN106588937; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 27825-20-3, name is Methyl 3-Hydroxy-2-pyrazinecarboxylate, 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 27825-20-3, Recommanded Product: Methyl 3-Hydroxy-2-pyrazinecarboxylate

Reference Example 27 0.30 g of methyl 3-hydroxy-2-pyrazinecarboxylate was dissolved in 1.5 ML of dimethyl sulfoxide, and thereafter, 0.70 ML of triethylamine and 0.54 g of L-aspartic acid diethyl ester hydrochloride were successively added thereto, followed by stirring at room temperature for 8 hours.. After chloroform and water were added to the reaction solution, the mixture was adjusted to PH 2 with 2 mol/L hydrochloric acid, and the organic layer was separated.. The obtained organic layer was washed with water and then dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure.. Toluene and n-hexane were added to the obtained residue, and the precipitate was collected by filtration, so as to obtain 0.18 g of diethyl (2S)-2-{[(3-hydroxy-2-pyrazinyl)carbonyl]amino} butanedioate.1H-NMR(CDCl3)delta: 1.27(3H,t,J=7.2Hz), 1.30(3H,t,J=7Hz), 2.94(1H,dd,J=4.4,17.2Hz), 3.15(1H,dd,J=4.8,17.2Hz), 4.14-4.23(2H,m), 4.24-4.32(2H,m), 4.99-5.02(1H,m), 8.15(1H,d,J=2.6Hz), 8.40(1H,d,J=1.5Hz), 8.78(1H,d,J=5.9Hz), 12.4(1H,brs)

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; TOYAMA CHEMICAL CO., LTD.; EP1417967; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63286-28-2, 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. 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, This compound has unique chemical properties. The synthetic route is as follows.

2-Chloro-3-hydrazinylpyrazine (710 mg, 0.49 mmol) obtained by the method described in WO2008/130951 was dissolved in acetonitrile (12 mL), and 1,1′-carbonyldiimidazole (1.6 g, 9.8 mmol) was added thereto, and then, the resulting mixture was stirred at room temperature for 4 hours. To the reaction mixture, water was added, and the deposited solid was collected by filtration, whereby the title Compound R7 (117 mg, yield: 14%) was obtained. 1H-NMR (400 MHz, DMSO-d6, delta): 13.2 (br s, 1H), 7.93 (d, J=4.0 Hz, 1H), 7.34 (d, J=4.0 Hz, 1H)

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-3-hydrazinylpyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KYOWA HAKKO KIRIN CO., LTD.; ISHIDA, Hiroshi; MOTOSAWA, Keiichi; MIURA, Yusuke; NAKAI, Ryuichiro; OKADA, Ryoko; TAKAHASHI, Yuichi; (45 pag.)US2016/168125; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 21943-12-4, name is 2-Amino-3-bromopyrazine, 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 21943-12-4, Recommanded Product: 21943-12-4

A suspension of 2-amino-3-bromopyrazine (2.5 g, 19.3 mmol) in DME (20 mL) was added 3-bromo-1, 1, 1-trifluoroacetone (13.7g, 72.Ommol) and 4A molecular sieves (1.0 g). The reaction mixture was then stined at 90 C for 4h and quenched by the addition of water (25mL).This mixture was extracted with ethyl acetate. The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to give 8-chloro-2-trifluoromethyl-imidazo [1,2-a] pyrazine (0.8g, 25%). ?H NMR (400 MHz, CDC13): oe 8.13- 8.10 (m, 2H), 7.84-7.82 (m, 1H); LC-MS: 268.3.0 [M+2Hj.

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-3-bromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; KOTRABASAIAH UJJINAMATADA, Ravi; PANDIT, Chetan; (152 pag.)WO2016/185342; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, 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. Quality Control of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine

2-Fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoic acid 1a (323 mg, 1.08 mmol) was dissolved in 5 mL of N, N-dimethylformamide, followed by addition of O-(1-benzotriazolyl)-N, N, N’, N’-tetramethyluronium hexafluorophosphate (614 mg, 1.63 mmol), 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine 4c (200 mg, 1.63 mmol) and N, N-diisopropylethylamine (0.4 mL, 2.16 mmol). After stirring for 12 hours, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by thin layer chromatography with elution system A to obtain 4-[[3-(6,8-dihydro-5H-imidazo[1,2-a]pyrazine-7-carbonyl)-4-fluoro-phenyl]methyl]-2H-phthalazin-1-one 4 (10 mg, yield 2.3%) as a white solid. MS m/z (ESI): 404.1 [M+1] 1H NMR (400 MHz, CDCl3): delta 10.07 (br. s, 1H), 8.53 (d, 1H), 7.96 (m, 1H), 7.83 (m, 3H), 7.51 (m, 1H), 7.30 (m, 2H), 6.01 (t, 1H), 4.73 (d, 2H), 4.35 (s, 2H), 1.60 (m, 2H), 1.34 (m, 2H)

The synthetic route of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hansoh Pharmaceutical Co., Ltd.; TANG, Pengcho; LI, Xin; LI, Xiangqin; CHEN, Yang; WANG, Bin; ZHU, Zhe; EP2604610; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 87885-43-6, name is 2-Chloro-3-nitropyrazine, 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 87885-43-6, COA of Formula: C4H2ClN3O2

EXAMPLE 2 1-(3-Nitro-2-pyrazinyl)hexahydro-1H-1,4-diazepin-5-one To a solution of hexahydro-1H-1,4-diazepin-5-one (1.14 g, 10 mmol) and triethylamine (1.01 g, 10 mmol) in isopropanol (30 ml) cooled in an ice bath, was added over 30 minutes a solution of 2-chloro-3-nitropyrazine (1.59 g, 10 mmol) in chloroform (20 ml). After addition was complete, the reaction mixture was allowed to warm to 20-25 and was stirred at this temperature for 20 hours. Solvents were removed under reduced pressure and the residue was partitioned between a saturated aqueous solution of sodium chloride and ethyl acetate. The ethyl acetate extract was dried over anhydrous sodium sulfate, filtered and concentrated to an oil. Flash chromatography over silica gel and elution with 2% methanol -98% chloroform gave pure 1-(3-nitro-2-pyrazinyl)hexahydro-1H-1,4-diazepin-5-one. STR3

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; Merck & Co., Inc.; US4619927; (1986); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4774-14-5, name is 2,6-Dichloropyrazine, 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 4774-14-5, SDS of cas: 4774-14-5

In a 250 mL flame dried RBF equipped with a temperature probe was added nBuLi (2.46 M, 2.2 mL, 5.39 mmol) and THF (49 mL) under nitrogen. The solution was cooled at -20 oC and 2,2,6,6-tetramethylpiperidine (0.95 mL, 5.64 mmol) was added dropwise. The solution was stirred at 0 oC for 30 min. before cooling at -105 oC with a nitrogen/Et2O bath. A – 78 C solution of 2,6-dichloropyrazine (730 mg, 4.90 mmol) in THF (16 mL) was then cannulated over 10 min. to the -105 C LiTMP solution. The mixture was allowed to stir an additional 30 min. at -100/-105 C and a -78 C solution of 2-chlorobenzaldehyde (0.83 mL, 7.35 mmol) in THF (7 mL) was added. The resulting solution was allowed to stir at -95 C for an additional 1h15. An aqueous saturated solution of NH4Cl (10 mL) was then added and the mixture was allowed to warm at room temperature. Water (200 mL) was added and the mixture was extracted with Et2O (3 x 50 mL). Combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtrated and the volatiles were removed under reduced pressure. The resulting residue was purified by silica gel chromatography (5 to 18% gradient of EtOAc/hexanes) to give (2-chlorophenyl)(3,5-dichloropyrazin-2-yl)methanol (1.10 g, 78% yield) as a yellow oil.1H NMR (500 MHz, CDCl3) delta ppm 8.56- 8.56 (m, 1H), 7.41 (dd, J = 7.7, 1.5 Hz, 1H), 7.27 (td, J = 7.4, 1.8 Hz, 1H), 7.23 (td, J = 7.5, 1.4 Hz, 1H), 7.12 (dd, J = 7.6, 1.8 Hz, 1H), 6.47 (d, J = 7.2 Hz, 1H), 4.07 (d, J = 7.2 Hz, 1H). MS (ES+) m/z 271/273/275 (MH-H2O)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichloropyrazine, and friends who are interested can also refer to it.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; ALBRECHT, Brian K.; GIORDANETTO, Fabrizio; GREISMAN, Jack, Benjamin; MARAGAKIS, Paul; TAYLOR, Alexander M.; WALTERS, W. Patrick; (117 pag.)WO2018/57884; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 13515-06-5,Some common heterocyclic compound, 13515-06-5, name is 5,6-Dimethylpyrazine-2-carboxylic acid, molecular formula is C7H8N2O2, 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.

5,6-dimethylpyrazine acid (about 0.27 mmol, prepared as Example 2), EDCI (0.35mmol) and DMAP (0.027mmol) were dissolved in dry methylene chloride (20mL), the chlorinated hederagenin(152 mg, 0.27 mmol, prepared as Example 4) was then dissolved in dichloromethane (20 ml). It was dropped into 5,6-dimethylpyrazine acid solution within 20 minutes, and stirred at room temperature for 12 hours. It was then diluted with dichloromethane (20 mL), washed with saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to obtain a white powder, H-23. Yield: 36% (afterchromatograph with DCM / MeOH, 1% -2%) as a white powder, m.p .: 123.6 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Dimethylpyrazine-2-carboxylic acid, its application will become more common.

Reference:
Patent; Xinhuo Zhiyao (Beijing) Technology Co., Ltd.; Fang Kang; Guo Wenbo; Wang Penglong; Cheng Gang; (26 pag.)CN110964078; (2020); A;,
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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H2ClN3

Step 1: [6-(3-Cyano-pyrazin-2-yloxy)-l-hydroxy-4-methyl-l,3-dihydro- benzo[c] [ 1 ,2] oxaborol-3-yl] -acetic acid ethyl ester I *- CCfeEt[0598] To a solution of ethyl 2-(l ,6-dihydroxy-4-methyl- 1 ,3-dihydrobenzo[c] [ 1 ,2] oxaborol-3-yl)acetate (1.0 g, 4.0 mmol) and S-chloro-pyrazine^-carbonitrile (0.84 g, 6.0 mmol) in DMF (24 mL) was added cesium carbonate (2.68 g, 8.8 mmol). The mixture was heated to 8O0C for 2 hrs. The reaction was cooled down, diluted withH2O, acidified to pH 3 with aqueous HCl (IN). The mixture was extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by column chromatography (silica, Hexanes/Ethyl acetate = 1 : 4) affording the title compound (1.30 g, 92%) as a white solid. 1H NMR (CDCl3) delta 8.40 (d, IH), 8.29 (d, IH), 7.36 (d, IH), 7.11 (d, IH), 5.69 (dd, IH), 4.81 (s, IH), 4.20 (q, 2H), 3.11 (dd, IH), 2.44 (dd, IH), 2.39 (s, 3H), 1.26 (t, 3H). MS found: (M+H)+ = 354.

The synthetic route of 55557-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; GLAXOSMITHKINE LLC; XIA, Yi; ALLEY, Michael, Richard Kevin; ZHOU, Yasheen; SINGH, Rajeshwar; DING, Charles; CAO, Kathy; PLATTNER, Jacob, J.; OU, Ligong; JIA, Guofeng; SARASWAT, Neerja; RAMACHANDRAN, Sreekanth; ZHOU, Ding; WO2011/17125; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem