Pyrazines

Reference of 41110-33-2,Some common heterocyclic compound, 41110-33-2, name is Methyl 5-methylpyrazine-2-carboxylate, 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.

Example 13-2 Synthesis of 5-bromomethyl-2-methoxycarbonylpyrazine (Compound IV-3) The compound obtained in Example 13-1 (500 mg) was dissolved in carbontetrachloride (10 ml) and N-bromosuccinimido (585 mg) and azobisisobutylonitrile (54 mg) were added. After stirring for 20 hours over an oil bath at 70C, the reaction mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography (14 g, chloroform/ethyl acetate = 2/1) to obtain the title compound (328.7 mg) as pale yellow syrup. MS(EI,Pos.):m/z=229,231[M+1]+ 1H-NMR(500MHz,DMSO-d6):delta=4.06(3H,s),4.62(2H,s),8.83(1H,d, J=1.5Hz),9.26(1H,d,J=1.5Hz).

The synthetic route of 41110-33-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1273571; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 88625-24-5, name is 5-Chloropyrazine-2-carbaldehyde, 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 88625-24-5, Product Details of 88625-24-5

2,2,2-Trif[uoro-N-methy[ethanamine [CAS RN: 2730-67-8] (254 mg, 2.25 mmo[,1.6 eq), 5-ch[oropyrazine-2-carba[dehyde [CAS RN: 88625-24-5] (200 mg,1 .40 mmo[, 1 .0 eq) and sodium triacetoxyborohydride (952 mg, 4.49 mmo[,3.2 eq) were suspended in 20 mL 1,2-dichioroethane. Then, triethylamine (0.39mL, 2.81 mmo[, 2.0 eq) was added and the reaction mixture was stirred at rt overnight. Then, water was added. After stirring for 10 mm, the resulting phases were separated by the use of a Whatman filter. The volatile components of the organic phase were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/ethyl acetate9/1 -> hexane/ethyl acetate 1/1) to give 100 mg (29% yield of theory) of the title compound.UPLC-MS (Method 1): R = 1.13 mm; MS (EI0): m/z = 240 [M+H].1H-NMR (400 MHz, DMSO-d6): oe [ppm] = 2.39 (5, 3H), 3.37 (q, 2H), 3.92 (5, 2H),8.50 (d, 1H), 8.74 (d, 1H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 486460-20-2, name is 3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-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 486460-20-2, Recommanded Product: 486460-20-2

A mixture of compound 10 (12.0 g, 0.064 mol) and the catalyst,Pd/C (10% w/w, 120.0 mg) in methanol (MeOH)(120 mL) was charged into an autoclave (500 mL) at ambienttemperature. The reaction mass was agitated for 24 h bymaintaining 3.5-4.5 Kg/cm2 hydrogen pressure at 40-45 C.The completion of reaction was judged by TLC. The reactionmass was concentrated under reduced pressure afterremove the Pd/C catalyst by passing through celite undernitrogen atmosphere. The residue was dissolved in IPA(24.0 mL) and then IPA.HCl (24.0 mL) was added slowly at 0-5 C. The precipitated solid was separated by filtration,after one hour agitation of the reaction mass, to obtain 3-trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyrazinehydrochloride (11) as a white crystalline solid (12.1 g, 82.9%).m.p.: 237-249 C (Lit. 236-246 C reported in chemical book).1H NMR (400MHz; DMSO-d6), d, ppm (J, Hz): 3.65 (2H, t,J5.6, Piperazine); 4.46 (2H, t, J5.6, Piperazine); 4.61(2H, s, Piperazine); 10.58 (2H, br, NH2). 13C NMR(100MHz; DMSO-d6) d, ppm (J, Hz): 39.09 (-CH2-CH2-),40.14 (-CH2-CH2-), 40.90 (-CH2-), 117.17 (d, J268.4, CF3),142.29 (C triazole), 148.73 (C triazole). LC-MS m/z (rel, %):193.08 (M+H)+ (100).

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-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mannam, Madhava Rao; Devineni, Subba Rao; Pavuluri, Chandra Mouli; Chamarthi, Naga Raju; Kottapalli, Raja Sekhara P.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 194; 9; (2019); p. 922 – 932;,
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Related Products of 54608-52-5, 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. 54608-52-5, name is 2-Hydrazinopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step B: Preparation of (la/?,5a/?)-2-(Pyrazin-2-yl)-la,2,5,5a-tetrahydro-li/-2,3- diaza-cyclopropa[a]pentalene-4-carboxylic Acid Ethyl Ester. [Method ClTo a stirred suspension of 2-ethoxy-2-oxo-l-((lLambda,5i?)-2-oxobicyclo[3.1.0]hexan-3- ylidene)ethanolate (300 mg, 1.28 mmol) in ethanol (5 mL) was added 2-hydrazinylpyrazine (141 mg, 1.28 mmol) followed by 6 N HCl (0.5 mL, 3.0 mmol). The reaction was stirred overnight at room temperature. The reaction was diluted with H2O and extracted with DCM. The combined organic phases were washed with H2O, dried over MgSO4, and concentrated. Purification by silica gel flash chromatography gave the title compound (150 mg). LCMS mlz = 271.2 [M+H]+; 1H NMR (400 MHz, CDCl3) delta ppm 0.47 (td, J= 4.7 and 3.4 Hz, IH), 1.22-1.28 (m, IH), 1.39 (t, J= 7.1 Hz, 3H), 2.26-2.30 (m, IH), 2.77-2.82 (m, IH), 2.87 (d, J= 16.6 Hz, IH), 2.98 (dd, J = 16.6 and 6.3 Hz, IH), 4.40 (q, J = 7.1 Hz, 2H), 8.40 (dd, J= 2.6 and 1.5 Hz, IH), 8.51 (d, 7= 2.5 Hz, IH), 9.39 (d, J = 1.3 Hz, IH).

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

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; THORESEN, Lars; JUNG, Jae-Kyu; STRAH-PLEYNET, Sonja; ZHU, Xiuwen; XIONG, Yifeng; YUE, Dawei; WO2011/25541; (2011); A1;,
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Synthetic Route of 4774-14-5, A common heterocyclic compound, 4774-14-5, name is 2,6-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

Example 4; 6-Chloro-N-phenylpyrazin-2-amine A solution of 2,6-dichloropyrazine (1 g, 6. 7 mrnol) and anitine (1. 25 g, 13.4 mmol) in ethoxyethanol (20 mE) containing DIPEA (2.5 mL, 13. 4 minor) was heated at reflux for 3 days under Na. The solution was concentrated under reduced pressure and the residue dissolved in EtOAc (50 mL) and washed successively with H20 (50 mL), 1M HC1 (2 x 50 mL), H20 (50 mL) and brine (50 mL). After drying (Na2SO4) the solvent was removed under reduced pressure and the residue chromatographed cluting with EtOAc-hexane (20:80-50:50) to separate pure product from the lower fractions (230 mg, 17%).

The synthetic route of 4774-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CYTOPIA RESEARCH PTY LTD; WO2005/66156; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 15986-92-2,Some common heterocyclic compound, 15986-92-2, name is 5,6-Dimethyl-2,3-dihydropyrazine, molecular formula is C6H10N2, 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 5, 6-dimethyl-2, 3-dihydropyrazine (2.3 g, 21 mmol) in absolute ethanol (60 mL) was added sodium metal (6.5 g, 280 mmol) in small portions over a 3 hour period. The resulting mixture was heated to reflux. After 3 hours at reflux, the product was distilled from the mixture while 200 mL of water was added gradually to reaction vessel. The distillate was treated with 1 N aqueous HCI solution and concentrated in vacuo to afford a semi-solid. Titration with acetone afforded 0.78 g (20% yield) of (trans)-2, 3- dimethylpiperazine, a compound of formula (Gb), as an orange solid ; NMR (DMSO-d6) 9.8 (br s, 4), 3.5- 3.2 (m, 6), 1.2 (s, 6) ppm.

The synthetic route of 15986-92-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING AKTIENGESELLSCHAFT; HORUK, Richard; WO2005/79769; (2005); A2;,
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Pyrazine | C4H4N2 – PubChem

Application of 14508-49-7, These common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, 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.

Step B: Preparation of 2-Hydrazinylpyrazine.Under nitrogen atmosphere, 2-chloropyrazine (96 mL, 1073 mmol) was added dropwise to 35 wt aqueous hydrazine (544 mL, 6009 mmol) at 65 C over 1 h. After the addition, stirring was continued at 63-67 C for 16 h and the reaction mixture was let stand at room temperature for two days. The mixture was filtered to remove a small amount of precipitate, then extracted with 10% iPrOH/dichloromethane (5 x 250 mL). The combined organic extracts were dried (MgS04), filtered, then concentrated under reduced pressure. The resulting solid was triturated with isopropyl acetate (600 mL). The solid was collected by filtration, rinsed with isopropyl acetate, then dried in vacuo to give the title compound (60 g) as a pale yellow solid. LCMS m/z = 111.2 [M+H]+; lU NMR (400 MHz, DMSO- ) delta 4.21 (s, 2H), 7.70 (d, 7 = 2.8 Hz, 1H), 7.89 (s, 1H), 7.93 (dd, 7 = 2.8, 1.5 Hz, 1H), 8.10 (d, 7 = 1.5 Hz, 1H).

The synthetic route of 14508-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; THATTE, Jayant; BLACKBURN, Anthony C.; HAN, Sangdon; JONES, Robert M.; JUNG, Jae-Kyu; MONTALBAN, Anthony Garrido; PAL, Biman B.; RUETER, Jaimie Karyn; STRAH-PLEYNET, Sonja; THORESEN, Lars; XIONG, Yifeng; YUE, Dawei; ZHU, Xiuwen; WO2012/116279; (2012); A1;,
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Application of 88625-24-5, These common heterocyclic compound, 88625-24-5, name is 5-Chloropyrazine-2-carbaldehyde, 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.

Step 2. To the residue from Step 1 was added solid sodium bicarbonate (1012 mg, 5 equiv) and 5-chloropyrazine-2-carbaldehyde (400 mg, 1.2 equiv) and DMF (8 mL). The mixture was stirred at 60 C for 18 hours then cooled and poured into water and the mixture neutralized with 1 M HCl. Extraction first with ether then with ethyl acetate gave an organic fraction that was washed four times with water, then dried on anhydrous sodium sulfate, filtered and concentrated in vacuo to give an orange solid that was carried forward crude: [MH]+ m z 318.

The synthetic route of 88625-24-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CERNAK, Timothy, A.; BALKOVEC, James, M.; NARGUND, Ravi, P.; REITER, Maud; SPERBECK, Donald, M.; DYKSTRA, Kevin, D.; YU, Yang; DREHER, Spencer; MALONEY, Kevin, M.; WU, Zhicai; DEVITA, Robert, J.; VERRAS, Andreas; WO2012/9217; (2012); A1;,
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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 1422772-78-8 as follows. HPLC of Formula: C7H4BrN3O2

Ice bath,(COCl) 2 (7.5 mL) and DMF (0.4 mL)Was slowly added dropwise to a solution of 2-bromo-5H-pyrrolo [2,3-b] pyrazine-7-carboxylic acid (60%, 4.00 g, 8.26 mmol) in dichloromethane (150 mL)Reaction at room temperature for 2 h. Concentrated under reduced pressure,The residue was dissolved in dichloromethane (120 mL)Cyclobutylamine (2.2 mL, 26 mmol) and triethylamine were added(2.4 mL) was added and the reaction was carried out overnight. The reaction was quenched with water (150 mL)Dichloromethane (150 mL x 3), and the organic layer was dried over anhydrous Na2SO4, (Eluent: Cl2CH2 / MeOH (v / v) = 30/1) to give 1.20 g of a tan solid Rate: 49.0%.

According to the analysis of related databases, 1422772-78-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd; Liu, Bing; Huang, Jiuzhong; Zhang, Yingjun; Xue, Yaping; Xing, Wei; Xu, Juan; Wu, Zuping; Yu, Tianxi; (106 pag.)CN106432246; (2017); A;,
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Application of 27825-21-4, 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. 27825-21-4, name is Methyl 3-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A solution of methyl 3-chloropyrazine-2-carboxylate (200.0 mg, 1.15 mmol, CAS 27825-21-4), (i?)-/V-[(3ri)-l,3-dihydrospiro[indene-2,4′-piperidin]-3-yl]-2-methylpropane-2- sulfmamide (772.0 mg, 1.26 mmol, 50% purity) and CsF (522.0 mg, 3.44 mmol) in DMSO (15.0 mL) was stirred at 60 C for 1 hour. The reaction mixture was poured into H20 (60.0 mL) and extracted with EtOAc (60.0 mL x 2). The combined organic layers were washed with brine (40.0 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give an orange residue. The residue was purified by flash silica gel chromatography (12 g column, ethyl acetate in petroleum ether from 0% to 65%) to give methyl 3-[(3ri)-3-{[(i?)-2-methylpropane-2-sulfmyl]amino}-l,3-dihydrospiro[indene-2,4′- piperidin]-l’-yl]pyrazine-2-carboxylate (450.0 mg, 89% yield) as a yellow oil. LCMS m/z [M+H]+= 443.1.

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

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
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