Month: September 2021

Electric Literature 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.

(e) (2S,5R)-benzyl5-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-2-(hydroxymethyl)piperidine-1-carboxylate To a solution of (3S,6S)-1-((benzyloxy)carbonyl)-6-(hydroxymethyl)piperidine-3-carboxylic acid (0.78 g, 2.66 mmol) in 20 mL of DMF was added HATU (1.21 g, 3.2 mmol). After stirring for 30 min under N2, (3-Chloro-pyrazin-2-yl) methanamine hydrochloride (0.48 g, 2.66 mol) and Et3N (0.8 g, 7.98 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours under N2. The mixture was partitioned between EA and water. The organic layer was washed with 1 N HCl and water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford (2S,5R)-benzyl 5-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-2-(hydroxymethyl) piperidine-1-carboxylate (0.7 g, 63.0% yield). 1HNMR (400 MHz, CD3OD): delta=8.50?8.54 (m, 1H), 8.35 (d, J=2.4 Hz, 1H), 7.31?7.41 (m, 5H), 5.16 (s, 2H), 4.63 (s, 2H), 4.34?4.38 (m, 1H), 4.21?4.25 (m, 1H), 3.72?3.77 (m, 1H), 3.63?3.67 (m, 1H), 3.01?3.07 (m, 1H), 2.46?2.54 (m, 1H), 1.80?1.93 (m, 3H), 1.61?1.71 (m, 1H). MS (ESI): M/Z (M+1): 419.1.

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 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 (0.27 mmol, prepared as Example 2), EDCI (0.35mmol) And DMAP (0.027 mmol) were dissolved in dry methylene chloride (20 mL). The compound hederagenin alcohol (140 mg, 0.27 mmol, prepared as Example 3) was dissolved in dichloromethane (20 mL). This solution was dropped into 5,6-methylpyrazine acid solution within 20 minutes, and stirred at room temperature for 12 hours. The reaction mixture was then diluted with dichloromethane (20 mL), washed with saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain a white powder, H-11. Yield: 25% (after chromatograph with DCM / MeOH, 1% -2%) as a white powder, m.p .: 146.2 C.

The synthetic route of 13515-06-5 has been constantly updated, and we look forward to future research findings.

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

Application of 38557-71-0, These common heterocyclic compound, 38557-71-0, name is 2-Chloro-6-methylpyrazine, 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.

To a suspension of 2-chloro-6-methylpyrazine (24 g, 186.7 mmol) in anhydrous MeOH (240 mL) was added NaOMe (12.1 g, 224 mmol). The mixture was stirred at 60-70C for 16hours. The mixture was cooled and filtered. The filtrate was concentrated in vacuo to give 2- methoxy-6-methylpyrazine (22 g, 95% yield). 1H NMR (CDCI3400 MHz): 7.98 (s, 1H), 7.94(s, 1H), 3.91 (s, 3H), 3.40 (s, 3H). LC-MS: tR = 1.47 mm (method 14), mlz= 124.8 [M + H].

Statistics shows that 2-Chloro-6-methylpyrazine is playing an increasingly important role. we look forward to future research findings about 38557-71-0.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2016/174188; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 41110-29-6, These common heterocyclic compound, 41110-29-6, name is Methyl 3-methylpyrazine-2-carboxylate, 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.

To a solution of methyl 3-methylpyrazine-2-carboxylate (9.1 g, 59.8 mmol) in DCM (100 mL) at 0 C., was added urea hydrogen peroxide adduct, 97% (7.81 g, 83 mmol) and trifluoroacetic acid anhydride (10.8 ml, 78 mmol) dropwise. The resulting mixture was stirred at 0 C. for 1 h, and at room temperature for 18 h. The reaction was diluted with DCM and quenched with saturated Na2SO3 solution; the aqueous layer was back-extracted with DCM. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude mixture was purified with ISCO (20% to 80% EtOAc/Hexanes) to afford a mixture of products: 2-(methoxycarbonyl)-3-methylpyrazine 1-oxide (5.2 g, 51.7% yield) and 3-(methoxycarbonyl)-2-methylpyrazine 1-oxide. The mixture was taken to next step without further purification.

The synthetic route of 41110-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WHITE, Ryan; ALLEN, Jennifer R.; EPSTEIN, Oleg; HONG, Fang-Tsao; HUA, Zihao; HUMAN, Jason Brooks; LOPEZ, Patricia; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; TAMAYO, Nuria A.; ZHENG, Xiao Mei; US2014/213581; (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. 4858-85-9, name is 2,3-Dichloropyrazine, A new synthetic method of this compound is introduced below., Formula: C4H2Cl2N2

To a solution of 2,3-dichloro-pyrazine (10 g) (commercially available) and N,N- dimethylformamide (“DMF”) (80 ml) was added diethylmalonate (26.87 g) and potassium carbonate (23.19 g). The reaction mixture was heated to 1 10C for 8 hours. The reaction mixture was cooled to ambient temperature, filtered and the filtrate concentrated. The residue was purified by chromatography on silica gel (eluent 5-95% ethyl acetate in isohexane) to give 2-(3-Chloro-pyrazin-2-yl)-malonic acid diethyl ester (12.93 g). 1 H- NMR (400MHz, CDCI3): 8.50 (s, 1 H), 8.40 (s, 1 H), 5.20 (s, 1 H), 4.30 (q, 4H), 1.30 (t, 6H) ppm.

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; SYNGENTA LIMITED; SYNGENTA PARTICIPATIONS AG; AVERY, Alaric; DE MESMAEKER, Alain; MULHOLLAND, Nicholas; WILLETTS, Nigel; WORTHINGTON, Paul; WO2012/62531; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 356783-16-9, name is 3,6-Dichloropyrazine-2-carbonitrile, 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 356783-16-9, Safety of 3,6-Dichloropyrazine-2-carbonitrile

KF (1 g, 6 eq) and TBAB (372.3 mg, 0.4 eq) were dissolved in a mixed solvent of toluene (10 ml) and dimethylsulfoxide (5 ml)After azeotropic removal of water,Compound 6 (500 mg, 1 eq) was added,55 ‘C conditions,Stir for 3 h.TLC shows the raw material reaction is complete,After falling to room temperature,30% H2O2 (0.35 ml) was added under ice bath,Reaction at 27 C for 2 h, add water (1 ml) andNaHCO3 (0.132 g, 1.57 mmol),50 reaction 8.5h,Ice bath with 6N HCl,Adjust pH = 1.0,Ethyl acetate (4 x 5 ml)The organic layer was washed twice with saturated brine,Dried over anhydrous sodium sulfate,The organic solvent was distilled off,Recrystallization from 20 times ethanol (crude weight ratio of ethanol to 1: 5 to 30)Obtained as white solid 7 (favipiravir),The yield was 65% (from the reactants6 is calculated).mp: 175-177 C.

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; Central South University; Liu Fengliang; Li Cuiqin; (19 pag.)CN106866553; (2017); A;,
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. 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Bromo-5-chloropyrazin-2-amine

3-Bromo-5-chloropyrazin-2-amine (200 mg, 0.96 mmol), triethylamine (290 mg, 2.88mmol), cuprous iodide (5 mg, 0.33 mmol) and palladium(II)bis(triphenylphosphine) dichloride(13 mg, 0.02 mmol) were dissolved in tetrahydrofuran (5 mL). The mixture was stirred at rt, thentrimethylsilylacetylene (0.15 mL, 1.06 mmol) was added dropwise to the mixture. After theaddition, the reaction mixture was warmed to 55 oc and stirred for 1 h. The reaction mixture wascooled to rt, and diluted with ethyl acetate (50 mL). The mixture was filtered. The filtrate wasconcentrated in vacuo, and the residue was purified by silica gel column chromatography(PE/EtOAc (v/v) = 3011) to give the title compound as a light yellow solid (208 mg, 96 %).MS (ESI, pos. ion) m/z: 227.00 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 7.98 (s, 1H), 5.11 (s, 2H), 0.31 (s, 9H).

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; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (303 pag.)WO2018/108125; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

87486-34-8, Adding some certain compound to certain chemical reactions, such as: 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, 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 87486-34-8.

A solution of 3,5-dibromo-1-methylpyrazin-2-one (500.0 mg, 2.46 mmol), NH3H2O (5.0 mL) in dioxane (30.0 mL) was heated at 105° C. for 20 h. The mixture was concentrated, diluted with EtOAc (50 mL) and filtrated to give the title compound (300.0 mg, 79.0percent) which was carried on without purification. LCMS (M+H)+ 204.

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 87486-34-8.

Reference:
Patent; Bennett, Michael John; Betancort, Juan Manuel; Boloor, Amogh; Kaldor, Stephen W.; Stafford, Jeffrey Alan; Veal, James Marvin; US2015/111885; (2015); 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. 957230-70-5, name is 3,6-Dibromopyrazin-2-amine, A new synthetic method of this compound is introduced below., name: 3,6-Dibromopyrazin-2-amine

Step 2 5 ,8-Diotabromo-3-methyliotamiotadazo[ 1 ,2 ajpyrazine[00298] 2,5-Dibromo-3-aminopyrazme (2 0 g, 7 9 mmol), 2-bromo-l,l -dimethoxypropane (7 25 g, 40 0 mmol) and py?dimum p-toluenesulfonate (2 0 g, 7 9 mmol) are stirred in acetomtrile (65 mL) at reflux for 3 days The mixture is cooled and the solvent evaporated under reduced pressure The residue is partitioned between DCM (150 mL) and water (50 mL) and the layers separated The organic fraction is washed with NaHCtheta3 (sat aq , 50 mL) and b?ne (50 mL) and d?ed over MgStheta4 Evaporation of the solvent under reduced pressure gives a viscous black oil (2 14 g) which is purified by silica chromatography, elutmg with 10% – 20% EtOAc in cyclohexane to afford the title compound as a red-brown solid (280 mg, 1 mmol)

The synthetic route of 957230-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5049-61-6, These common heterocyclic compound, 5049-61-6, name is Pyrazin-2-amine, 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.

General procedure: In a stainless reactor bomb, the respective aromatic amine (1.0mmol), 4c (0.50 mol%), K2CO3 (5.0 mol%), and MeOH (1.0 mL) were placed. Then, the reactor was sealed with a stainless stopper, and the mixture was stirred for 17 h at 120 C. After removing MeOH under reduced pressure, the products were isolated by silica gel column chromatography.

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

Reference:
Article; Toyooka, Genki; Tuji, Akiko; Fujita, Ken-Ichi; Synthesis; vol. 50; 23; (2018); p. 4617 – 4626;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem