Month: May 2021

Related Products of 2727-13-1, 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. 2727-13-1, name is 3-Amino-6-chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

DIPEA (200 muIota, 1.15 mmol) was added to a solution of 3-amino-6-chloropyrazine-2- carboxylic acid (50 mg, 0.29 mmol), 2-(aminomethyl)-1-ethyl-6-methoxy-3-methyl-1H-1 ,3- benzodiazol-3-ium iodide, Intermediate 13 (100 mg, 0.29 mmol) and HBTU (142 mg, 0.37 mmol) in anhydrous DMF (1 ml). The resulting mixture was stirred at ambient temperature for 18 h. The reaction mixture was concentrated under a flow of nitrogen to afford the crude product as an oil. The crude material was purified by flash column chromatography on C18 (12 g). The column was eluted with MeCN:H20 + 0.1 % formic acid using the following gradient (%MeCN, column volumes): 10%, 2 CV; 10-100%, 20 CV; 100%, 2 CV. The desired fractions were combined and lyophilised to yield the product as an off-white solid (84 mg, 58%).1H NMR (250 MHz, DMSO-de) delta 9.57 (t, J = 5.3 Hz, 1 H), 8.38 (s, 1 H), 7.93 (d, J = 9.1 Hz, 1 H), 7.66 (s, 2H), 7.57 (d, J = 2.2 Hz, 1 H), 7.29 (dd, J = 9.1 , 2.3 Hz, 1 H), 4.99 (d, J = 5.3 Hz, 2H), 4.62 (q, J = 7.0 Hz, 2H), 4.09 (s, 3H), 3.91 (s, 3H), 1.38 (t, J = 7.1 Hz, 3H). LC/MS (System C): m/z (ESI+) = 375 [M(35CI)+], 377 [M(37CI)+]), R = 1.83 min, UV purity = 100%.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-6-chloropyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 24241-18-7, These common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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.

5-Bromopyrazine-2,3-diamine (27) was preparedfrom 2-amino-3,5-dibromopyrazine and NH4OH (25%) in sealedtube according to lit.33 1H-NMR delta ppm (CD3OD): 4.90 (s,4H,NH2),7.24 (s,2H,H-5,6). 13C-NMR (CD3OD): 123.3, 129.8, 144.3, 145.9. MS(ESI+) m/z: 189(M + H, 100%), 191(M + H+2, 97%). 27 (0.303 g,1.6 mmol) in EtOH (10 mL) was reduced by hydrogenation using 40psi of H2 and 10% Pd-C (15 mg) for 8 h. The catalyst was filtered ona bed of Celite, the filtrate was concentrated in vacuo. Purplecolored powder 28 were used for the further steps without purification.1H-NMR delta ppm (CD3OD): 4.90 (s,4H,NH2), 7.24 (s,2H, H-5,6). 13C-NMR (CD3OD): 123.7, 145.1. MS (ESI) m/z: 110(M + H,100%). 29 was prepared from 28 (0.11 g) and Na2S2O5 adduct of 4-(morpholin-4-ylcarbonyl) benzaldehyde (0.323 g) as described ingeneral method. Resulting precipitate (0.155 g) was purified withcolumn chromatography using CH2Cl2: MeOH (95 : 5) as eluant,yield 0.056 g, (18%), mp > 300 C. 1H-NMR delta ppm (DMSO-d6+D2O):3.27-3.61 (m,8H), 7.62 (d,2H,J – 8.4 Hz), 8.33 (d,2H,J – 8.4 Hz), 8.40(s,2H,H-5,6). 13C-NMR (DMSO-d6+D2O): 66.0, 127.3, 127.8, 129.9,138.2, 139.0, 154.7, 168.2. MS (ESI) m/z: 310(M + H, 100%). AnalCalcd for C16H15N5O2H2O: C, 58.70; H, 5.23; N, 21.39. Found: C,58.97; H, 5.01; N, 20.91.

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karaaslan, Cigdem; Doganc, Fatima; Alp, Mehmet; Koc, Asli; Karabay, Arzu Zeynep; Goeker, Hakan; Journal of Molecular Structure; vol. 1205; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 54608-52-5, 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. 54608-52-5, name is 2-Hydrazinopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

To 2-hydrazinopyrazine (2 g, 18.16 mmol) was added isonicotinic acid (pyridine-4- carboxylic acid, 4.47 g, 36.3 mmol, commercially available e.g. from Sigma-Aldrich or Allichem LLC) followed by polyphosphoric acid (50 mL), and the reaction was stirred at 155 0C for 18 hours. The hot solution was added to ice and neutralised by addition of ammonia 0.88. The aqueous solution was then extracted with ethyl acetate (3 extractions), washed with brine, and dried. The yellow solid thus obtained was treated with Dichloromethane, and any remaining solid material was filtered off and put to one side. The filtrate was evaporated and the residue was purified by chromatography using 0-10% of methanol in Dichloromethane as eluent. The fractions containing the product were evaporated to give ~260mg of yellow solid which was combined with the material set aside earlier to give 0.538 g of 3-(4- pyridinyl)[1 ,2,4]triazolo[4,3-a]pyrazine. LCMS: [M+H]+ = 198 retention time = 0.35 minutes (2 minute method)

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

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (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. 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., name: 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

(3R)-3-[(l,l-Dimemylethoxycarbonyl)ammo]-4-(2,4,5-trifluorophenyl)butanoic acid (10 g) is mixed with 4-(4,6-dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholinium chloride (10 g) in methanol (100 ml) at the laboratory temperature. 3-(Trifluoromethyl)-5,6,7,8-tetrahydro- [l,2,4]triazolo[4,3-a]pyrazine hydrochloride (7 g) is added to the resulting solution and triethylamine (4.7 ml) is added to the stirred suspension. During 2-3 minutes a solution is obtained that is further stirred at the laboratory temperature. After approximately 1 hour, white suspension of the product starts to separate. The reaction mixture is heated up to 50C and distilled water (35 ml) is added to the resulting solution and the reaction mixture is cooled down to 15C under stirring during 2 h. The separated product is filtered off and washed with 15 ml of a methanol/water (2/ 1 ) mixture. After drying the desired product is obtained with the yield of 96% and HPLC quality of >99%. Example 2

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 762240-92-6.

Reference:
Patent; ZENTIVA, K.S.; RICHTER, Jindrich; HALAMA, Ales; JIRMAN, Josef; WO2014/86325; (2014); 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. 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

Preparation of Intermediate I-70 To a solution of Intermediate I-02 (150 mg, 0.58 mmol) in Toluene (6.8 mL), 2-chloro-1,1-dimethoxypropane (0.758 mL, 5.8 mmol) and p-toluensulfonic acid (18 mg, 0.09 mmol) were added. The reaction mixture was refluxed for 24 h and additional amounts of 2-chloro-1,1-dimethoxypropane (10 eq) and p-toluensulfonic acid (0.16 eq) were added. The reaction mixture was refluxed for 15 h and the solvent was removed. The residue was purified by column chromatography (Isolute 10 g; AcOEt-cyclohexane 0:100 to 50:50) to give the Intermediate I-70 (55 mg, 32%) as a beige solid.

According to the analysis of related databases, 117719-17-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Centro Nacional De Investigaciones Oncologicas (CNIO); US2012/83492; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 957230-70-5, These common heterocyclic compound, 957230-70-5, name is 3,6-Dibromopyrazin-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.

Step 1: To a solution of 3,6-dibromopyrazin-2-amine (504 mg, 2 mmol) and 2, 2,6,6-tetramethylpiperidin-4-amine (0.35 mL, 2 mmol) in EtOH (2 mL) was added DIEA (0.38 mL, 2 mmol). The reaction mixture was subjected to microwave irradiation at 180 C for 3.5 h. The reaction mixture was cooled and concentrated. The residue was purified by silica gel column chromatography eluting with a MeOH (2.5% NH40H)/CH2Cl2 gradient (0-30% MeOH/NH4OH) to provide 5-bromo-N2-(2, 2, 6, 6-tetramethylpiperidin-4-yl)pyrazine-2, 3-diamine (0.35 g, 54%). MS m/z 328.0, 330.0 [M+H]+.

Statistics shows that 3,6-Dibromopyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 957230-70-5.

Reference:
Patent; PTC THERAPEUTICS, INC.; SYDORENKO, Nadiya; ALAM, Md Rauful; ARNOLD, Michael A.; BABU, Suresh; BHATTACHARYYA, Anuradha; CHEN, Guangming; GERASYUTO, Aleksey I.; KARP, Gary Mitchell; KASSICK, Andrew J.; MAZZOTTI, Anthony R.; MOON, Young-Choon; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; WOLL, Matthew G.; YAN, Wuming; ZHANG, Nanjing; (0 pag.)WO2020/5873; (2020); 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. 87597-21-5, name is Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate

Intermediate 1-07 (1.00 g, 2.87 mmol) was dissolved in DCM (28 mE) and N-bromosuccinimide (0.61 g, 3.44 mmol) and trifluoroacetic acid (0.25 mE) were added. The reaction mixture was stirring at rt for 16 h and then heated at 60 C. for 2 h more. The reaction mixture was cooled, andwashed with watet The organic phase was dried (Na2SO4), filtered and the solvent removed in vacuum. The residue was purified by biotage with a gradient cyclohexane/EtOAc:from 100% to 50:50 The desired fractions were collected to obtained 1.15 g of a white solid as intermediate 1-09 (Y:94%).

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; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); Serrano Marugan, Manuel; Pastor Fernandez, Joaquin; Martinez Gonzalez, Sonia; Ortega Molina, Ana; Bischoff, James R.; Oyarzabal Santamarina, Julen; (220 pag.)US9993554; (2018); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1049026-49-4, A common heterocyclic compound, 1049026-49-4, name is 2-Bromo-5-(methylthio)pyrazine, molecular formula is C5H5BrN2S, 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: 2-bromo-5-(methylsulfonyl)pyrazine: An aqueous solution of Oxone (4.0 g, 6.6 mmol,3.13 mL) was added dropwise to a methanol solution of 2-bromo-5-(methylsulfanyl)pyrazine(450 mg, 2.2 mmol, 19 mL) at ambient temperature. The reaction mixture was stirred for 3hours, filtered over a pad of CELITE and then organic layer was concentrated in vacuo. The crude residue was purified via MPLC (0-100% EtOAc/hexane gradient) to afford titlecompound.

The synthetic route of 1049026-49-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP; TANG, Haifeng; PIO, Barbara; JIANG, Jinlong; PASTERNAK, Alexander; DONG, Shuzhi; FERGUSON, Ronald Dale, II; GUO, Zack Zhiqiang; CHOBANIAN, Harry; FRIE, Jessica; GUO, Yan; WU, Zhicai; YU, Yang; WANG, Ming; WO2015/17305; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 63286-28-2, These common heterocyclic compound, 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, 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 3-chloro-2-hydrazinopyrazine (3.0 g, 20.75 mmol), prepared from 2,3-dichloropyrazine and hydrazine using a procedure analogous to that described in the literature (Huynh-Dinh et al, J. Org. Chem. 1979, 44, 1028), was added 8 mL of triethyl orthopropionate. After refluxing for 10 h, the reaction was cooled down to ambient temperature and the precipitate was filtered. The solid was purified by flash chromatography (100% ethyl acetate, then 10% methanol in ethyl acetate) to give 2.73 g of the title compound as a solid. 1H NMR (500 MHz, CDCl3) delta 1.54 (t, 3H, J=7.6 Hz), 3.16 (q, 2H, J=7.8 Hz), 7.70 (d, 1H, J=4.5 Hz), 7.83 (d, 1H, J=4.8 Hz)

Statistics shows that 2-Chloro-3-hydrazinylpyrazine is playing an increasingly important role. we look forward to future research findings about 63286-28-2.

Reference:
Patent; Merck Sharp & Dohme Corp.; Edmondson, Scott D.; Fisher, Michael H.; Kim, Dooseop; Maccoss, Malcolm; Parmee, Emma R.; Weber, Ann E.; Xu, Jinyou; US2015/359793; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 87486-33-7, These common heterocyclic compound, 87486-33-7, name is 3,5-Dichloro-1-methylpyrazin-2(1H)-one, 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: 6?-Chloro-4?-methyl-4-(2-trifluoromethyl-benzoyl)-3,4,5,6-tetrahydro-2H,4?H-[1,2?]bipyrazinyl-3?-one (1)[0262][0263]Compound 1 is prepared according to synthesis method 1: 1.76 g (5.97 mmoles) of derivative 1 h and 1.13 g (6.31 mmoles) of pyrazinone 4c are placed in 3 ml of butanol-1 in the presence of 4 ml (27.9 mmoles) of NEt3. This mixture is stirred at 120 C. for 24 hours. After concentrating the reaction medium to dryness, the residue obtained is taken up with AcOEt and washed with water and with a saturated NaCl solution. After drying on MgSO4, the organic phase is concentrated to dryness. The residue obtained is purified by silica flash chromatography (CH2Cl2-AcOEt gradient: 100-0 to 90-10). 0.86 g of beige solid is isolated (yield: 36%).[0264]TLC silica gel 60 F 254 Merck, CH2Cl2-MeOH: 95-5, Rf=0.71.[0265]F=162 C.[0266]1H NMR (CDCl3) ppm: 3.28 (t, 2H, J=5.18 Hz), 3.44 (s, 3H), 3.67-3.88 (m, 3H), 3.93-4.09 (m, 3H), 6.73 (s, 1H), 7.35 (d, 1H, J=7.6 Hz), 7.54 (t, 1H, J=7.6 Hz), 7.62 (t, 1H, J=7.6 Hz), 7.73 (d, 1H J=8 Hz).[0267]MS (+ESI) m/z 401 (MH+)

Statistics shows that 3,5-Dichloro-1-methylpyrazin-2(1H)-one is playing an increasingly important role. we look forward to future research findings about 87486-33-7.

Reference:
Patent; PIERRE FABRE MEDICAMENT; Leroy, Isabelle; Dupont-Passelaigue, Elisabeth; Mialhe, Samuel; Junquero, Didier; Valeille, Karine; US2013/40928; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem