Month: May 2021

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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, A new synthetic method of this compound is introduced below., Quality Control of 2-Bromo-5-iodopyrazine

To a 250 ml_ flask were added 2-bromo-5-iodopyrazine (2.9 g, 10 mmol, 1 equiv.), di- te/f-butyl-9H-carbazole (3.0 g, 11 mmol, 1.1 equiv.), copper powder (640 mg, 10 mmol, 1 equiv.) and potassium carbonate (4.5 g, 30 mmol, 3 equiv.). The flask was degassed by three cycles of vacuum-nitrogen purging and 50 ml_ of chlorobenzene was injected. The mixture was stirred at 110 C for 10 h under a nitrogen atmosphere. After cooling, water was added to the reaction mixture followed by extraction with DCM (3 c 50 ml_). The combined organic layers were dried with anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and the crude product was purified by silica gel column chromatography. DCM/Hexane=1/3 was used as eluent to afford Br-Pz-tCz as a faint yellow solid. Yield: 85%. Rf: 0.65 (33% DCM/Hexanes). Mp: 180-182 C. 1H NMR (400 MHz, CDCI3) d (ppm): 8.84 (d, J = 1.4 Hz, 1 H), 8.74 (d, J = 1.4 Hz, 1 H), 8.13 (dd, J = 2.0, 0.6 Hz, 2H), 7.84 (dd, J = 8.8, 0.7 Hz, 2H), 7.54 (dd, J = 8.7, 2.0 Hz, 2H), 1.49 (s, 18H). 13C NMR (101 MHz, CDCI3) d (ppm): 147.97, 145.94, 145.28, 139.30, 137.06, 134.57, 125.10, 124.37, 1 16.46, 1 10.73, 34.85, 31.87. HR-MS (LTQ Orbitrap XL) [M+H]+ Calculated: (Cz^z/NsBr) 436.1383, 438.1363; Found: 436.1380, 438.1359

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; UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; ZYSMAN-COLMAN, Eli; CHEN, Dongyang; PACHAI GOUNDER, Rajamalli; (104 pag.)WO2019/202342; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 768-05-8, name is Pyrazinoic acid hydrazide, 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 768-05-8, COA of Formula: C5H6N4O

To a stirred solution of hydrazide (3) (12 mmol) and KOH (10.8 mmol) in ethanol (25 mL), carbon disulde (CS2) (13.2 mmol) was slowly added. Then, the resulting mixture was stirred at room temperature for 8 h until the (4) precipitated from the solvent, collected using suction filtration and dried, and followed by recrystallization in ethanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Pyrazinoic acid hydrazide, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Fei; Wen, Qing; Wang, She-Feng; Shahla Karim, Baloch; Yang, Yu-Shun; Liu, Jia-Jia; Zhang, Wei-Ming; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 90 – 95;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 23611-75-8, The chemical industry reduces the impact on the environment during synthesis 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

1.78 g (10.31 mmol) of methyl 6-chloropyrazine-2-carboxylate synthesized by the method described in Non Patent Literature 1 was dissolved in 20 ml of methylene chloride. To this solution, 1.47 g (17.60 mmol) of O-ethylhydroxylammonium chloride was added. Thereafter, 21.5 ml (1.0 M, n-hexane solution, 21.5 mmol) of trimethylaluminum was added dropwise under nitrogen atmosphere and ice cooling, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and Celite filtration was carried out. Then it was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the inorganic matter was removed by filtration. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2.08 g (10.31 mmol, yield 100%) of 6-chloro-N-ethoxypyrazine-2-carboxamide.

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, Methyl 6-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NIPPON SODA COMPANY LIMITED; ITO, SYUICHI; AMANO, TOMOHIRO; IPPOSHI, JUNJI; KOUBORI, SHINYA; (44 pag.)JP2016/30742; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 24241-18-7 as follows. name: 2-Amino-3,5-dibromopyrazine

Step 1. 3-amino-6-bromopyrazine-2-carbonitrileA mixture of NaCN (140 mg, 2.85 mmol) and copper (I) cyanide (255 mg, 2.85 mmol) in anhydrous DMF (13 mL) was stirred at 120 C. for 20 min under an atmosphere of N2. To the resulting clear solution was added drop-wise a solution of 3,5-dibromopyrazin-2-amine (from Aldrich; 800 mg, 3.16 mmol) in DMF (4.8 mL) and stirring was continued at 120 C. The reaction was held at 120 C. for 40 h at which time LCMS analysis indicated complete conversion. The reaction was cooled to ambient temperature and partitioned between water and EtOAc, the phases were separated and the aqueous phase was washed with additional EtOAc. The combined organic phase was washed with water followed by brine, then dried over MgSO4 and concentrated in vacuo to provide the crude product, 597.1 mg, which was used without any further purification.

According to the analysis of related databases, 24241-18-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rodgers, James D.; Shepard, Stacey; Arvanitis, Argyrios G.; Wang, Haisheng; Storace, Louis; Folmer, Beverly; Shao, Lixin; Zhu, Wenyu; Glenn, Joseph; US2010/298334; (2010); 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. 4774-14-5, name is 2,6-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H2Cl2N2

j0671j To a solution of tert-butyl azetidin-3-ylcarbamate hydrochloride (LXIII) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture was added 2,6-dichloropyrazine (LXIV) (1.428 g, 9.58 mmol) and the reaction was stirred at 95C for 3 h. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous Na2504, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes-*hexanes:EtOAc 1:1) to yield tert-butyl (1-(6-chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXV) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C12H17C1N402 mlz 285.1 (M+H).

According to the analysis of related databases, 4774-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (254 pag.)WO2017/23993; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 762240-92-6, 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. 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of 3-(trifluoromethyl)-5,6,7,8-tetrahydro [1,2,4]triazolo[4,3-a]pyrazine hydrochloride salt (1.0 eq.) in dimethylformamide(DMF, 2-3 mL)was added potassium carbonate (2.5eq.) at and stirred for 15 min at room temperature. To this, N-(benzo[d]thiazol-2-yl)-2-chloroacetamide derivatives (1.0 eq.) in DMF was added to the reaction mixture at room temperature. The resulting reaction mixturewas heated at 70 C for 18 h. The completion of the reaction was monitored on TLC (using 10% MeOH: DCM and ammonia as a modifier as mobile phase) which confirmed that the reaction got completed after 18 h. The reaction mixture was pouredinto ice-cold water and extracted with ethyl acetate (2 x 30 mL).Organic layers were combined and the combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford crude desired product and crystallized it from methanol to get N-(benzo[d]thiazol-2-yl)-2-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo [4,3-a]pyrazin-7 (8H)-yl)acetamide derivatives(12a-12e) in good practical yield.

The chemical industry reduces the impact on the environment during synthesis 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Jethava, Divya J.; Acharya, Prachi T.; Vasava, Mahesh S.; Bhoi, Manoj N.; Bhavsar, Zeel A.; Rathwa, Sanjay K.; Rajani, Dhanji P.; Patel, Hitesh D.; Journal of Molecular Structure; vol. 1184; (2019); p. 168 – 192;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 356783-16-9, 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. 356783-16-9, name is 3,6-Dichloropyrazine-2-carbonitrile belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(a) In 1.1 L of dimethyl sulfoxide was suspended 90.1 g of 3,6-dichloro-2-pyrazinecarbonitrile. After adding 180.5 g of potassium fluoride and 66.8 g of tetra-n-butylammonium bromide, the mixture was stirred at 50-55 C. for 6 hours. The reaction mixture was returned to room temperature and added to a mixture of 1.1 L of ethyl acetate and 2.2 L of water, and the organic layer was separated. Water (1 L) was added to the organic layer, pH was adjusted to 2.5 with 1 mol/L hydrochloric acid, and the organic layer was separated. The organic layer was washed with saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography [eluent: n-hexane:ethyl acetate=10:1] to obtain 58.3 g of 3,6-difluoro-2-pyrazinecarbonitrile as a colorless solid product. R (KBr) cm-1: 2250 H-NMR (CDCl3) delta: 8.34(1H,dd,J=1.3, 7.9 Hz)

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, 3,6-Dichloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Toyama Chemical Co., Ltd.; US2003/130213; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

5049-61-6, name is Pyrazin-2-amine, 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. Computed Properties of C4H5N3

A mixture of pyrazin-2-amine (2) (1.0 equiv.) and ethyl 3-bromo-2-oxopropanoate (3) (1.5 equiv.) in ethanol (15 mL)was exposed to microwave irradiation at 200 W intermittently at 10 s intervals for 30 min at 150 C. On completion of reaction as indicated by TLC, the reaction mixture was cooled, concentrated and treated with cold water. Reaction mass was concentrated completely under reduced pressure. Obtained crude was purified by column chromatography on 100-200 silica gel by eluting 50 % ethyl acetate in n-hexane, to get off pale brown compound 4, yield: 90 %; m.p. 151-153 C. IR (KBr, numax, cm-1): 3352, 3081, 3009, 2959, 2918, 1748, 1612, 1426, 1426,1353, 1276, 1254, 903, 813; 1H NMR (400 MHz, DMSO-d6):delta 1.28 (t, 3H, CH3), 3.85 (q, 2H, CH2), 4.62 (brs, 1H, NH); LC-MS: m/z 192.06 [M+H] +. Anal. calcd. (%) for C9H9N3O2:C 56.54, H 4.74, N 21.98. Found (%): C 56.65, H 4.76, N22.03.

The synthetic route of 5049-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jyothi, Boggavarapu; Madhavi, Nannapaneni; Asian Journal of Chemistry; vol. 32; 1; (2020); p. 84 – 90;,
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. 41110-29-6, name is Methyl 3-methylpyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 3-methylpyrazine-2-carboxylate

A solution of methyl 3-methylpyrazine-2-carboxylate (9.1 g, 59.8 mmol) in DCM (100 mL) was cooled to 0 C. was added urea hydrogen peroxide adduct (7.8 g, 83.0 mmol), followed by dropwise addition of trifluoroacetic acid anhydride (10.8 mL, 78.0 mmol). The resulting mixture was stirred at 0 C. for 1 h, and at RT for 18 h, during which LCMS indicated a mixture of two peaks corresponding to MS m/z=169.0 [M+H]+. The reaction was diluted with DCM and quenched with saturated Na2SO3 solution; the aqueous layer was back-extracted with DCM (2×). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. ISCO purification (20-80% EtOAc/hexanes) afforded a mixture of two regioisomers, containing 3-(methoxycarbonyl)-2-methylpyrazine 1-oxide and 2-(methoxycarbonyl)-3-methylpyrazine 1-oxide (5.2 g, 30.9 mmol, 51.7% yield). The mixture of regioisomers was taken to next step without further purification. MS m/z=169.0 [M+H]+. A solution of the mixture of 3-(methoxycarbonyl)-2-methylpyrazine 1-oxide and 2-(methoxycarbonyl)-3-methylpyrazine 1-oxide (5.1 g, 15.2 mmol) in toluene (50 mL) was cooled to 0 C. and phosphorus oxychloride (2.8 mL, 30.3 mmol) was added under nitrogen followed by DMF (0.12 mL, 1.52 mmol). The reaction mixture was stirred at RT for 4 h, and heated to 65 C. for 18 h, cooled to RT, diluted with EtOAc and washed with saturated NaHCO3 solution. The aqueous layer was back-extracted with EtOAc (2×). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. ISCO purification (0-50% EtOAc/hexanes) with care afforded both isomers: methyl 5-chloro-3-methylpyrazine-2-carboxylate (0.68 g) (minor product) denoted by peak 1 and methyl 6-chloro-3-methylpyrazine-2-carboxylate (1.50 g) (major product) denoted by peak 2. MS m/z=187.0 [M+H]+. Peak 1: 1H NMR (300 MHz, DMSO-d6) delta 8.73 (s, 1H), 3.91 (s, 3H), 2.71 (s, 3H). Peak 2: 1H NMR (300 MHz, DMSO-d6) delta 8.89 (s, 1H), 3.91 (s, 3H), 2.71 (s, 3H).

According to the analysis of related databases, 41110-29-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 944709-42-6, name is 6,8-Dibromo-[1,2,4]triazolo[1,5-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 944709-42-6, SDS of cas: 944709-42-6

6,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine (8.68 g, 31.2 mmol) was dissolved in DMF (84mL). To this was added (1r,4r)-ethyl 4-(4-amino-1H-pyrazol-1-yl)cyclohexanecarboxylate(7.41 g, 31.2 mmol) and triethylamine (8.70 mL, 62.5 mmol). The reaction mixture was stirredat ambient temperature for 17 h. The reaction mixture was then added to ice water (200 mL) and extracted with EtOAc (200 mL). The organic layer was dried over MgSO4, filtered, andconcentrated to provide the title compound (13.2 g, 97percent). MS m/z: 436, 434 (M+H)+. 1HNMR (400 MHz, DMSO-d6) delta 10.66 (s, 1H), 8.56 (d, J = 6.2 Hz, 2H), 8.10 (s, 1H), 7.80 (s, 1H),4.27±4.13 (m, 1H), 4.08 (q, J = 7.1 Hz, 2H), 2.40 (ddd, J = 12.3, 8.8, 3.4 Hz, 1H), 2.14±1.96 (m,4H), 1.86±1.70 (m, 2H), 1.62±1.47 (m, 2H), 1.20 (t, J = 7.1 Hz, 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:
Article; George, Dawn M.; Huntley, Raymond J.; Cusack, Kevin; Duignan, David B.; Hoemann, Michael; Loud, Jacqueline; Mario, Regina; Melim, Terry; Mullen, Kelly; Somal, Gagandeep; Wang, Lu; Edmunds, Jeremy J.; PLoS ONE; vol. 13; 9; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem