Tag: M.W=100-200

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. 4774-15-6, name is 2,6-Dimethoxypyrazine, A new synthetic method of this compound is introduced below., Quality Control of 2,6-Dimethoxypyrazine

General procedure: Representative procedure for the preparation of 1-phenoxycarbonyl-2-phenyl-3-methoxy-1,2-dihydropyrazine (3a). To a stirred solution of 2-methoxypyrazine (0.200 g, 1.816 mmol) inanhydrous THF (5 mL) was added phenylchloroformate (0.28 mL, 2.225 mmol) at 0 C andstirring was continued under nitrogen atmosphere until salt formation was completed (15 min, asdetermined by TLC on neutral alumina, EtOAc/hexanes 1:19). The reaction mixture was cooledto -41 C, a 1 M solution of phenylmagnesium bromide in THF (2.4 mL, 2.4 mmol) was addedand the mixture stirred until reaction completion (40 min, as determined by TLC on neutral SiO2,EtOAc/hexanes 1:9), and then quenched with 2 mL of aqueous 20% NH4OH/NH4Cl 1:1 (w/w).The mixture was extracted with dichloromethane (2 × 15 mL), dried over Na2SO4, andconcentrated in vacuo. Purification of the crude mixture by flash silica gel columnchromatography (0-15% EtOAc/hexanes) afforded 3a (0.488 g, 87%) as a white solid (3:2mixture of rotamers): mp: 81-82 C; 1H NMR (CDCl3, 500 MHz) delta 7.49-7.27 (m, 7H), 7.20 (t, J= 7.5 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 6.99 (d, J = 7.5 Hz, 1H), 6.67 and 6.63 (2d due torotamers, J = 5.5 Hz, 1H), 6.16 and 6.14 (2d due to rotamers, J = 5.0 Hz, 1H), 5.89 and 5.87 (2sdue to rotamers, 1H), 3.84 and 3.83 (2s due to rotamers, 3H); 13C NMR (CDCl3, 125 MHz) delta160.2, 160.0, 151.6, 151.5, 150.7, 150.4, 136.8, 135.9, 129.3, 128.8, 128.7, 128.6, 127.2, 126.6,125.9, 125.8, 121.3, 118.2, 118.1, 112.5, 111.8, 56.0, 54.6, 54.0, 53.9; HRMS (ESI) m/z calcdfor C18H17N2O3 [M + H]+ 309.12337, found 309.123554

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; St Hilaire, Valentine R.; Hopkins, William E.; Miller, Yenteeo S.; Dandepally, Srinivasa R.; Williams, Alfred L.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 72 – 78;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 16298-03-6, 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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Example 3a: methyl 3-amino-6-iodopyrazine-2-carboxylate 1.5 equivalents of N-iodosuccinimide are added at room temperature to 5 g (32.7 mmol) of a methyl 3-aminopyrazine-2-carboxylate solution in 25 ml of dimethylformamide. The reaction medium is heated at 65 °C for 1 hour, added together with 0.5 equivalents of N-iodosuccinimide and maintained at 65°C for 24 hours. After returning to room temperature, the solvent is evaporated and then the product is extracted several times with dichloromethane. The organic phases are combined, washed with 10percent sodium bisulfite solution, dried on magnesium sulfate and concentrated to yield 8 g (88percent>) of methyl 3-amino-6-iodopyrazine-2-carboxylate in the form of a yellow solid. LCMS (EI, m/z): (M+l) 280 1H NMR: deltaEta ppm (400 MHz, DMSO): 8.50 (1H, s, CHarom), 7.50 (2H, bs, NH2), 3.20 (3H, s, CH3).

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

Reference:
Patent; PIERRE FABRE MEDICAMENT; KRUCZYNSKI, Anna; CREANCIER, Laurent; KALOUN, El Bachir; BEDJEGUELAL, Karim; RABOT, Remi; WO2014/16434; (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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 939412-86-9

in a 3 L reaction flask, DCM (dichloromethane) (500 mL), intermediate 2 (39 g,217 mmol), 1148-11-4 (N-benzyloxycarbonyl-L-proline) (54 g, 217 mmol) and Et3N (87.7 g, 868 mmol) were addedsuccessively. Under nitrogen protection, the reaction solution was cooled to 0 C and HATU (2-(7-azobenzotriazole)-tetramethylurea hexafluorophosphate) (98.8 g, 260 mmol) was added in batches. The reaction solution wasnaturally warmed to room temperature, and the reaction was carried out for 14 hours under stirring. After the reactionwas completed, HCl (400 mL, 0.5 N H2O) was added, the obtained mixture was filtered through diatomite and wasextracted, the organic phase was washed with NaHCO3 (5%) and saturated saline solution, dried over Na2SO4 andconcentrated, then passed through column (PE (polyethylene): EA (ethyl acrylate) = 1:1) to obtain intermediate 3(12.7 g, yield: 14.7%) as a white solid. LCMS showed a molecular ion peak (M+1) 375.0.

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; Hangzhou Sanyintai Pharmaceutical Technology Co., Ltd.; Yin, Jianming; YIN, Jianming; LV, Yubin; LI, Bangliang; (36 pag.)EP3480199; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 768-05-8, name is Pyrazinoic acid hydrazide, 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. Recommanded Product: 768-05-8

General procedure: To a stirred solution of the acid hydrazide 5 (2mmol, 0.27g) in absolute ethanol (10ml), the appropriate heteroaromatic ketone or substituted pyrazolaldehyde (2mmol) was added in the presence of catalytic amount of glacial acetic acid (5 drops), the mixture was refluxed for 12-16h. The product obtained was filtered, washed with diethyl ether, dried and recrystallized from ethanol.

The synthetic route of Pyrazinoic acid hydrazide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hassan, Nayera W.; Saudi, Manal N.; Abdel-Ghany, Yasser S.; Ismail, Azza; Elzahhar, Perihan A.; Sriram, Dharmarajan; Nassra, Rasha; Abdel-Aziz, Marwa M.; El-Hawash, Soad A.; Bioorganic Chemistry; vol. 96; (2020);,
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. 486460-20-2, name is 3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine

Using Procedure G-3 (Table 5) with compound 478 the title compound 479 (crude) was obtained (130 mg, 89%) as a brown oil. MS (m/z): 193.1 (M+H)

The synthetic route of 486460-20-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Forum Pharmaceuticals, Inc.; Rogers, Kathryn; Patzke, Holger; (315 pag.)US2017/749; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 74290-69-0, name is 5-Bromo-6-methylpyrazin-2-amine, 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 74290-69-0, COA of Formula: C5H6BrN3

A suspension of 5-bromo-6-methylpyrazin-2-amine (500 mg, 2.66 mmol), sodium cyanide (1303 mg, 26.6 mmol), copper(l) cyanide (2382 mg, 26.6 mmol) in DMF (10 ml) was stirred at 120 C during 15 h. After cooling to rt, the reaction mixture was diluted with H20 (10 ml) and concentrated. The residue was partitioned between EtOAc (100 ml) and 3% ammonium hydroxide (150 ml). The aqueous layer was extracted further with EtOAc (2 x 70 ml), and the combined organic layers were washed again with 3% ammonium hydroxide (50 ml), brine (50 ml), dried (Na2S04), filtered and concentrated to give the title compound. [M+H]+ = 135.0, HPLC RtA= 0.75 min.

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; NOVARTIS AG; FLOHR, Stefanie; MARKERT, Christian; NAMOTO, Kenji; PIRARD, Bernard; WO2013/111108; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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 mixture of (cis)-2-((benzyloxy)carbonyl)-4-oxooctahydro-1H-pyrido[1,2-a]pyrazine-7-carboxylic acid (0.7 g, 2.1 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (450 mg, 2.5 mmol), HATU (1.2 g, 3.1 mmol) and TEA (0.85 g, 8.4 mmol) in DMF (10 mL) was stirred at 25 C. for overnight. Then the reaction mixture was poured into water, the mixture was extracted with EA (50 ml*3). The combined organic phase was washed with brine (100 mL), dried over Na2SO4, concentrated in vacuo, the residue was purified by silica gel column chromatography (PE/THF=1/3) to give (cis)-benzyl 7-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-4-oxohexahydro-1H-pyrido[1,2-a]pyrazine-2(6H)-carboxylate (440 mg, yield 45.8%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (3-Chloropyrazin-2-yl)methanamine hydrochloride, its application will become more common.

Reference:
Patent; KIM, RONALD M.; Liu, Jian; Gao, Xiaolei; Boga, Sobhana Babu; Guiadeen, Deodialsingh; Kozlowski, Joseph A.; Yu, Wensheng; Anand, Rajan; Yu, Younong; Selyutin, Oleg B.; Gao, Ying-Duo; Wu, Hao; Liu, Shilan; Yang, Chundao; Wang, Hongjian; US2014/206681; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 33332-25-1, 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 33332-25-1 as follows.

Example 95 [0308] [Formula 107]CI xj – ~ CI’ [0309] 1) In tetrahydrofuran (66 mL) was dissolved methyl 5-chloropyrazine-2-carboxylate (3.3 g), and 1M diisobutylaluminum hydride/hexane solution (38.3 mL) was added dropwise to the solution under nitrogen atmosphere at -70C or lower over 10 minutes, and the resulting mixture was further stirred for 10 minutes. At -60C or lower, 1M diisobutylaluminum hydride/hexane solution (31.3 mL) was added dropwise to the mixture over 20 minutes, and the mixture was further stirred at -70C or lower for 1 hour. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and after stirring at room temperature, filtered with Celite. The filtrate was extracted with ethyl acetate, washed with a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=100:0 to 80:20) to obtain 5-chloropyrazine-2-carbaldehyde (970 mg). MS (m/z): 142/144 [M+H]+

According to the analysis of related databases, 33332-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; SAKURAI, Osamu; SARUTA, Kunio; HAYASHI, Norimitsu; GOI, Takashi; MOROKUMA, Kenji; TSUJISHIMA, Hidekazu; SAWAMOTO, Hiroaki; SHITAMA, Hiroaki; IMASHIRO, Ritsuo; WO2012/81736; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

16298-03-6, name is Methyl 2-aminopyrazine-3-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. category: Pyrazines

(4.59 g ’30 mm O1), N – bromosuccinimide (5.34 g, 30 mm O1) and acetonitrile (1: 1) were added to the reactor, 0 0 mL), stirred overnight at room temperature, filtered, the filter cake washed with acetonitrile, and the filter cake was dried to give the title compound as a yellow solid.

The synthetic route of 16298-03-6 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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 16298-03-6

A solution of methyl 3-aminopyrazine-2-carboxylate (3.0 g, 19.6 mmol) and BS (3.5 g, 23.5 mol) in MeCN (70 mL) was stirred at 70°C for 5 h. Then the mixture was concentrated and extracted with EtOAc. The organic layer was washed with a2S03 (a.q.) and brine, dried over Na2S04 and concentrated in vacuo. The crude product of methyl 3-amino-6- bromopyrazine-2-carboxylate (3.0 g, yield: 92percent) was used for next step without further purification. -NMR (CDC13, 400 MHz) delta 8.18 (s, 1H), 6.54-6.93 (m, 2H), 3.86 (s, 3H). MS (M+H)+: 232 / 234.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16298-03-6.

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