Category: Pyrazines

Synthetic Route of 1379338-74-5, The chemical industry reduces the impact on the environment during synthesis 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, I believe this compound will play a more active role in future production and life.

tert-butyl 3-(aminomethyl)-3-fluoropiperidine-1-carboxylate (3.86 g, 16.6 mmol) and DIPEA (3.22 g, 24.9 mmol) were added to a solution of 5,7-dichloropyrido[3,4-b]pyrazine (3.32 g, 16.6 mmol) in THF (60 mL) and the mixture was refluxed overnight. The volatile components were evaporated and the residue was extracted with ethyl acetate. Ethyl acetate was washed with brine and dried. The solvent was removed in vacuo The crude residue was purified by silica-gel chromatography eluting with Hexane-50% EtOAc/Hexane (gradient) then C18 column to afford the subtitled compound as pale yellow solid 1.76 g. MS (m/z): 396 (M+H)+

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, 5,7-Dichloropyrido[3,4-b]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; Su, Wei-Guo; Deng, Wei; Ji, Jianguo; US2014/121200; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 55557-52-3, name is 3-Chloropyrazine-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 55557-52-3, category: Pyrazines

A mixture of the respective boronic acid derivative (B-B(OH)2) (21.5 mmol), 3-chloro- pyrazine-2-carbonitrile (21.5 mmol), a solution of K2CO3 (59.4 mmol) in water (30 ml_),PPh3 (3. 2 mmol), Pd(OAc)2 (1.05 mmol) in dry DME was stirred at reflux under inert atmosphere for 16 h. After cooling to rt, the reaction mixture was diluted with EtOAc, filtered over celite, the filtrate was dried over MgSO4, filtered and concentrated in vacuo to yield the desired pyrazine-2-carbonitrile derivative which was used for the next step without further purification3-m-Tolyl -pyrazine-2-carbonitrile prepared by reaction with commercially available 3-m-tolyl-boronic acid LC-MS: tR = 0.88 min; [M+H+MeCN]+ = 243.63

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-Chloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; HAZEMANN, Julien; KOBERSTEIN, Ralf; SIEGRIST, Romain; SIFFERLEN, Thierry; WO2010/4507; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 768-05-8, A common heterocyclic compound, 768-05-8, name is Pyrazinoic acid hydrazide, molecular formula is C5H6N4O, 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.

Potassium hydroxide 11.5 g (0.20 mol) was dissolved in absolute ethanol (400 mL) at ambient temperature. Then pyrazine-2-carbohydrazide (2) 40g (0.299 mole) added and reaction mass was cooled. Carbon disulfide 25.08 g (0.33 mol) added in small portions and the mixture was stirred at reflux temperature for 12 h. The reaction mixture changed to green colour with the evolution of hydrogen sulfide. The completion of reaction was monitored by TLC (Chloroform 9.5: Methanol 0.5). Ethanol completely distilled under vacuum below 50C. The reaction mass cooled to 25-30C. Water (100 mL) added to dissolve salts and pH 6.0-7.0 adjusted by conc. HCl (20 mL). Solid precipitated out. Stir at 25-30C for 1h, solid filtered, water (50 mL) washing given and dried to give white to off white solid compound (3) 36.32 g (70.00%). Thus yield obtained was used in the next step without further purification. mp- 208-210C. IR (KBr, cm-1): 3352.4 (-NH2 stretch), 3230.3 (>NH stretch), 2845 (-OCH3), 1640.65 (>C=O stretch), 764 (>C-Br); 1H NMR (400 MHz, DMSO-d6 ppm): delta 8.76 (s, 1H), 8.80 (s, 1H), 9.19 (s, 1H), 14.82 (s, 1H). 13C NMR (400MHz, DMSO-d6 ppm): 138.58 (pyrazine C-N), 143.45 (pyrazine C=N), 145.28 (pyrazine C=N), 147.29 (pyrazine C=N), 158.32 (-C=O), 178.48 (-C-SH). MS: 178.9; m/z: 179.9 (M+H).

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; Patil, Sanjeev R.; Asrondkar, Ashish; Patil, Vrushali; Sangshetti, Jaiprakash N.; Kalam Khan, Firoz A.; Damale, Manoj G.; Patil, Rajendra H.; Bobade, Anil S.; Shinde, Devanand B.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 16; (2017); p. 3845 – 3850;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature 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.

A mixture of Boc acid (1.8 gm, 0.005 moles) from Example 11 and carbomyldiimidazole (1.05 gm, 0.0064 moles) in ethylacetate (20ml) was reacted with 3-(trifluoromethyl)-5,6,7,8-tetrahydro[l,2,4]triazolo[4,3-a]pyrazine hydrochloride (Synthon 2) (1.48 gm, 0.0064 moles) at room temperature. The resulting reaction mass was heated to 50-55C for 15 hrs. After completion of reaction by TLC the reaction mass was quenched with water (18ml) at room temperature and cooled to 10-15C. The precipitated product was collected to give 2.2 gm of product. SOR (1% in methanol) +3.6 Melting point 189-192.8C Chiral purity by HPLC 99.30%

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:
Patent; SMILAX LABORATORIES LIMITED; MALLELA, Sambhu, Prasad, Sarma; HAVALE, Shrikant, Hanumantappa; BODDEPALLI, Nagabhushana, Rao; GUNJI, Nagarjuna; MOKKAPATI, Bhavani, Sankar; WO2013/114173; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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. HPLC of Formula: C8H10N2O

General procedure: New a, b-unsaturated carbonyl-based compounds (5a-g and 6au)were synthesized using direct coupling technique [40] (Scheme 1). The reaction was carried out using base-catalyzed Claisen-Schmidt condensation reaction, by reacting different types of ketoneswith appropriate aromatic aldehyde at molar ratio 2:1 tosynthesize new compounds (5a-g) and at molar ratio 1:1 for (6a-u).For synthesis of 6a-u first 5a-g intermediates were synthesized andin second step appropriate aldehydes were reacted with intermediates.The detailed method of synthesis has already beenreported by us previously [38,40]. Scheme 1 shows the highlights ofsynthesis of compound 3, 4 and a, b-unsaturated carbonyl-basedcompounds along with oxime derivatives. 15 mL ethanol wastaken in a round bottom flask and aromatic aldehyde (20 mmol, 2equivalent) and specific ketone (10 mmol,1 equivalent) were addedand dissolved using a stirrer for 2-3 min at 5 C. Into the abovesolution, 40% NaOH solution in ethanol was added drop wise andthe mixture was stirred for 1-24 h at 27 C. The color change andprecipitate formation in the reaction mixture showed productformation. TLC was used to monitor the reaction and acidified icewas added to quench the reaction once completed. The isolation ofcompounds was done by recrystallization and/or by using columnchromatography. 3.2.1. 2,6-Bis-(3,5,6-trimethyl-pyrazin-2-ylmethylene)-cyclohexanone (5a)Yield: 74%; Mp: 112e113 C; 1H NMR (500 MHz, CDCl3) d: 7.87 (s,2H), 2.55 (s, 6H); 2.51 (s, 6H); 2.48 (s, 6H); 2.37 (t, J 8.0 Hz, 4H),1.85 (m, 2H); 13C NMR (500 MHz, CDCl3) d: 181.2,152.7,150.4,149.6,147.9, 146.2, 141.4, 27.9, 27.1, 17.1, 16.8, 16.1; HRMS (ESI) m/z:363.4754 [MH], Microanalysis calculated for C22H26N4O(362.47), C: 72.90%, H: 7.23%, N: 15.46%. Found C: 72.96%, H: 7.25%,N: 15.42%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 186534-02-1, its application will become more common.

Reference:
Article; Zha, Gao-Feng; Qin, Hua-Li; Youssif, Bahaa G.M.; Amjad, Muhammad Wahab; Raja, Maria Abdul Ghafoor; Abdelazeem, Ahmed H.; Bukhari, Syed Nasir Abbas; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 34 – 48;,
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Pyrazine | C4H4N2 – PubChem

Application of 95-89-6, The chemical industry reduces the impact on the environment during synthesis 95-89-6, name is 3-Chloro-2,5-dimethylpyrazine, I believe this compound will play a more active role in future production and life.

[1-ETHYLPROPYLAMINE] (1.0 mmol) followed by sodium tert-butoxide (1.25 mmol) is added to a mixture of 2-chloro-3,6-dimethylpyrazine (0.83 mmol), tris (dibenzylideneacetone) dipalladium [(0)] (2 mol%), and BINAP (6 mol%) in ethyleneglycol dimethyl ether (2 mL) under nitrogen. The mixture is stirred at 70-80C for 2.5 hours, diluted with aqueous ammonium chloride, and extracted 1: 1 hexane-Et20. Combined extracts are dried (sodium sulfate), filtered, concentrated, and chromatographed on silica gel (10: 1 to 4: 1 hexane-EtOAc eluent) to give the aminopyrazine.

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-Chloro-2,5-dimethylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROGEN CORPORATION; WO2004/18437; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 13301-04-7, 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. 13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a dimethylformamide (160 ml) solution of 3,6-dibromopyrazine-2-carboxylic acid methyl ester (4.0 g, 13.5 mmol), 4-fluorothiophenol(1.36 ml, 12.8 mmol)) and potassium carbonate (1.86 g, 13.5 mmol) were added and the mixture was stirred for 2 hours at room temperature. The reaction solution was poured into water, extracted with ethyl acetate and washed (with water and brine, in this order), dried (over anhydrous magnesium sulfate), filtered and concentrated to obtain a residue, which was purified by silica gel column chromatography [developing eluent: hexane: ethyl acetate = 20:1 to 10:1] to obtain 6-bromo-3-[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester (1.62 g) in the form of colorless powder. MS (ESI/APCI Dual): 343 (M+1) 1H NMR (300 MHz, CDC13) delta ppm 4.06 (s, 3 H) 6.99 – 7.25 (m, 2 H) 7.41 – 7.59 (m, 2 H) 8.43 (s, 1 H)

The chemical industry reduces the impact on the environment during synthesis Methyl 3,6-dibromopyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Nissan Chemical Industries, Ltd.; EP2157090; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 762240-92-6, These common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, 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: 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.2.1.6.1. N-(benzo[d]thiazol-2-yl)-2-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)acetamide (12a). Solid, m. p.198-200 C; Anal. Calcd for C15H13F3N6OS: C, 47.12; H, 3.43; F,14.91; N, 21.98; O, 4.18; S, 8.39%; found C, 47.35; H, 3.65; N, 22.15; S,8.52%; IR (KBr) (numax, cm-1): 3089 (=C-Hstr), 2945 (C-Hstr), 1662(C=Ostr), 1587 (C=Cstr), 1326 (C-Nstr), 1203 (C-Fstr); 1H NMR(400 MHz, DMSO) delta 10.05 (s, 1H, -NH), 8.29-7.88 (m, 2H, C23 &C26), 7.56-7.39 (m, 2H, C24&25), 4.04 (dt, J= 8.6, 5.5 Hz, 2H, C10),3.82 (s, 1H, C6), 3.56 (d, J = 14.7 Hz, 2H, C2&6), 3.39 (s, 1H, C2), 3.10 (t,J =5.4 Hz, 1H, C9), 2.67 (t, J = 5.4 Hz, 1H, C9); 13C NMR (100 MHz,DMSO) delta 169.53 (C1), 153.43 (C19), 151.3 (C21), 144.39 (C5), 134.41(C22), 132.73 (C13), 124.30 (C14), 122.86 (C24), 121.34 (C23), 118.71(C26), 58.69, (C2), 52.34 (C6), 51.18 (C9), 43.09 (C10); ESI-MS (m/z):383.3 [M+1].

The synthetic route of 762240-92-6 has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 122-05-4,Some common heterocyclic compound, 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, molecular formula is C6H4N2O4, 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.

Sulfuric acid (19 mu, 0.36 mmol) was added to a methanol (1.2 mL, 29 mmol) solution of pyrazine-2,5-dicarboxylic acid (Ark Pharma cat AK-76746, 100 mg, 0.6 mmol). Then the mixture was allowed to stir at 90 C overnight. After cooling to rt, the mixture was diluted with methanol and basified with NaOH aq. Then the mixture was allowed to stir at rt for 5 h to reach -50% conversion to afford the mono-ester. Then the mixture was acidified with HC1 aq, and extracted with DCM/iPrOH x 3. The organic layer was dried and concentrated to afford desired product, which was used in the next step without further purification. LC-MS calculated for C7H7N2O4 (M+H)+: m/z = 183.0; found 183.0.

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

Reference:
Patent; INCYTE CORPORATION; WU, Liangxing; YU, Zhiyong; ZHANG, Fenglei; YAO, Wenqing; (173 pag.)WO2017/106634; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1458-18-0, The chemical industry reduces the impact on the environment during synthesis 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

Examples 66 and 67[0285] A suspension of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (25.0 gm, 0.113 moles) in 2-propanol (200 mL) was stirred as pyrrolidine (8.84 gm, 0.124 moles) was added. To this mixture was added diisopropyethylamine (16.3gm, 0.126 moles) after which the reaction was heated to reflux. At reflux, a brown solution resulted. After 2 hours at reflux, TLC (silica, 1 : 1 ethyl acetate and hexane) showed all of the starting material had been consumed with the formation of a single product. The reaction was cooled to room temperature which caused the product to crystallize. The solid product was isolated by filtration and was washed with 2- propanol and then with diethyl ether. After drying there was obtained 24.8 gm (85.5%) of the product as a pink solid.

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-amino-5,6-dichloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANUS BIOTHERAPEUTICS, INC.; LIPFORD, Grayson, B.; ZEPP, Charles, M.; WO2012/167046; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem