Category: 723286-80-4

These common heterocyclic compound, 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-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. category: Pyrazines

EXAMPLE 176; 7- {5- [(6,7-dichloro- 1-oxo- 1 ,2-dihydr opyr rolo [1 ,2-alphal pyrazin-4-yl)methyll -2- fluorobenzoyl}-3-pyrrolidin- l-yl-5,6,7,8-tetr ahydro [ 1 ,2,41 triazolo [4,3-alphal pyrazin-2-ium trifluoroacetate (AA2)Step 1: 3-Pyrrolidin-l-yl-5,6,7,8-tetrahydro[l,2,41triazolo[4,3-alphalpyrazin-7-ium trifluoroacetate (AAl)A mixture of tert-bvXy 3-bromo-5,6-dihydro[l,2,4]triazolo[4,3-alpha]pyrazine-7(8H)-carboxylate(0.231 mmol) in pyrrolidine (3 ml) was stirred overnight in a sealed tube at 6O0C. The volatiles were removed under reduced pressure and the resulting crude was diluted with DCM and washed with sat. aq. NH4Cl solution. The organic phase was dried (Na2SO4) and filtered. Evaporation of the solvent provided a crude which was dissolved in a mixture of DCM/TFA (1:1, 0.23 M) and stirred at room temperature for 30 min. The volatiles were removed under reduced pressure and the resulting crude was used as such in the next step without purification. MS (ES) C9H15N5 required: 193, found: 194 (M+H)+.

The synthetic route of tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2007/138355; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 723286-80-4,Some common heterocyclic compound, 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, molecular formula is C10H15BrN4O2, 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 1 ,1-dimethylethyl 3-bromo-5,6-dihydro[1 ,2,4]triazolo[4,3-a]pyrazine- 7(8H)-carboxylate (200 mg, 0.660 mmol, commercially available) in 1 ,4-dioxane (2 ml_), 2-(tributylstannanyl)pyridine (364 mg, 0.990 mmol) was added and mixture was degassed with a stream of argon for few minutes. Pd(Ph3P)4 (38.1 mg, 0.033 mmol) was then added followed by copper(l) iodide (39.2 mg, 0.206 mmol) and the mixture was submitted to microwave irradiation heating at 130 0C for 25 minutes until the reaction was complete by LCMS. Volatiles were removed under reduced pressure and the residue was purified by chromatography on silica gel (Snap 1 1 g NH column) eluting with a gradient from 0 to 100% ethyl acetate in iso-hexane (10CV) and then with 100% ethyl acetate (7CV). A colourless oil was obtained. The product was still impure and so was further purified by chromatography on silica gel (Si 5g) eluting with a 80% ethyl acetate in iso hexane (5CV) and then with 10% MeOH in DCM (5 CV) then by chromatography on silica gel (Si column 5g) eluting first with ethyl acetate (4CV) and then with 10% MeOH in DCM (6CV). Colourless oil was obtained of the desired product in 115 mg. LCMS m/z 301.9 [M+H] (at) 0.84 min (2 min run)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, its application will become more common.

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

Related Products of 723286-80-4, The chemical industry reduces the impact on the environment during synthesis 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, I believe this compound will play a more active role in future production and life.

The compound obtained in Step 4 (53 mg) was dissolved in chloroform (2 mL), trifluoroacetic acid (0.2 mL) was added and stirred overnight at room temperature. The oil obtained reaction solution by concentration under reduced pressure was dissolved in N, N- dimethylformamide (1.5 mL), Was stirred for 2 hours at 200 C. was added cesium carbonate (111 mg) and 4-fluoro-2- (trifluoromethyl) benzonitrile (64 mg). To the reaction solution was extracted 3 times with ethyl acetate after addition of water, The organic layer was washed with water and saturated brine, Dried and concentrated with sodium sulfate. The resulting residue to give the title compound purified by silica gel column chromatography (19mg, 30%). LRMS (ESI) m / z 372 [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, tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAIHO PHARMACEUTICAL COMPANY LIMITED; MINAMIGUCHI, KAZUHISA; OKAJIMA, SHIGEO; AOKI, SHINICHI; ASAI, MASANORI; ASAI, TAKAHIRO; YAMANAKA, HIROYOSHI; DOHI, SUGURU; (149 pag.)JP5851663; (2016); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 723286-80-4,Some common heterocyclic compound, 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, molecular formula is C10H15BrN4O2, 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 0.173 g (0.571 mmol) OF 3-BROMO-7- (TERT-BUTOXYCARBONYL)- 5,6, 7,8-tetrahydro [1, 2, 4] triazolo [4, 3-a] pyrazine in 6 ML of methanol was added 0. 39 ML of 25% w/w solution of sodium methoxide in methanol. The reaction was heated at 65 C for 1 d. The reaction was diluted with ethyl acetate and washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo. The crude product was purified by flash chromatography on a BIOTAGE system (silica gel, 5% methanol/ethyl acetate) to yield the title compound. LC/MS 255.1 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2004/58266; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, molecular formula is C10H15BrN4O2, 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. Product Details of 723286-80-4

3-Bromo-5,6-dihydro-8H-[l,2,4]triazolo[4,3-a]pyrazine-7-carboxylic acid tert- butyl ester (54.8 mg, 0.181 mmol), 4-(( ^)-3-mo holin-4-yl-l-phenylsulfanyl-methyl- propylamino)-3-trifluoromethanesulfonyl-benzenesulfonamide ( 100 mg, 0.181 mmol), (IS, 25)-N,N’-dimethyl-cyclohexane-l,2-diamine (07.71 mg, 0.054 mmol), cesium carbonate (100 mg, 0.307 mmol), and copper (I) iodide (5.16 mg, 0.027 mmol) were added to a microwave vial followed by toluene (2 mL). The reaction mixture was degassed for 15 minutes under nitrogen and then heated to 90C for 14 hours. The crude material was directly purified via flash chromatography on silica gel (0-25% 7 N ammonia in methanol in CH2C12) to afford the title compound (130 mg, 92% yield). MS [m/z; (M+l)+]: 776.5

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 723286-80-4, its application will become more common.

Reference:
Patent; NOVARTIS AG; MILLER-MOSLIN, Karen; TOURE, Bakary-Barry; VISSER, Michael Scott; YUSUFF, Naeem; WO2011/29842; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 723286-80-4, 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. 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A solution of tert-butyl 3-bromo-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylate (1 g, 3.30 mmol, 1 equiv.) in CH3NH2 (in EtOH) (7 mL) was stirred for 20 h at 100 degree Celsius. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The resulting mixture was concentrated under reduced pressure. The residue was purified by reverse phase flash with the following conditions (Column: C18 Column 120 g; Mobile Phase A: Water(10 mmol/L AcOH), Mobile Phase B: ACN; Flow rate: 50 mL/min; Gradient: 20% B to 50% B in 40 min; 254/220 nm) to afford tert-butyl 3-(methylamino)- 5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylate(550 mg, 65.82%) as a off-white solid.

The synthetic route of tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
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. 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, A new synthetic method of this compound is introduced below., Safety of tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate

A mixture of pyrazole (33.7 mg, 0.495 mmol) and sodium hydride (19.79 mg, 0.495 mmol) in Lambda/,Lambda/-dimethylformamide (DMF) (1 ml) was cooled to 0 0C and 1 ,1- dimethylethyl 3-bromo-5,6-dihydro[1 ,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (50 mg, 0.165 mmol, commercially available from e.g. Allichem, Ark Pharm or Bepharm) was added. After completion of the addition, the mixture was stirred at room temp for 30 mins and then at 1 10 0C. After 3 h, the DMF was evaporated and a few drops of NH4CI solution were added followed by ethyl acetate (50 ml). The solution was dried (Na2SO4), filtered and concentrated. The product was purified by MDAP to give desired product in 24.1 mg. LCMS MH+ = 291 (at) 0.79 min (2 min run)

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; 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

Electric Literature of 723286-80-4, A common heterocyclic compound, 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, molecular formula is C10H15BrN4O2, 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.

Preparation 154: 3-bromo-5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3-a]pyrazine To a solution of ie/i-butyl 3-bromo-5,6-dihydro-[1 ,2,4]triazolo[4,3-a]pyrazine- 7(8H)-carboxylate (52 mg, 0.172 mmol) in DCM (6 mL) at 0C was added TFA (0.26 mL). The reaction was stirred at room temperature for 16 hours before concentrating in vacuo. The residue was purified by elution through an SCX-2 column using 2M NHs/MeOH to give the title compound as yellow solid (29 mg, 83%). 1 H NMR (500 MHz, MeOD): delta 4.10 (s, 1 H), 3.93 (t, J = 5.63 Hz, 2H), 3.25 (t, J = 5.63 Hz, 2H). LCMS (ESI) Rt = 0.40 minutes MS m/z 203 [M79Br+H]+

The synthetic route of 723286-80-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; CHEUNG, Jack; ATRASH, Butrus; SHELDRAKE, Peter; WO2014/37751; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 723286-80-4, 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 723286-80-4 as follows.

A mixture of tert-butyl 3-bromo-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylate (1.65 mmol, 500 mg), 1-chloro-3-ethynyl-benzene ( 3.3 mmol, 450.5 mg, 0.406 mL), Pd tetrakis (0.083 mmol, 95.3 mg) and sodium acetate (3.3 mmol, 448.9 mg) in DMF anhydrous (10 mL) was stirred at 120C in a MW Biotage Robot 8 oven for 10 minutes, cooled to r.t., poured into water and extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed in vacuo and the crude residue was purified via automated flash chromatography (Biotage Isolera, SNAP25 cartridge) eluted with Petroleum ether/EtOAc gradient from 30% to 100% of EtOAc. (0197) The title product (280 mg, 47 % yield) was isolated as a pale yellow solid.

According to the analysis of related databases, 723286-80-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RECORDATI INDUSTRIA CHIMICA E FARMACEUTICA S.P.A; GRAZIANI, Davide; RIVA, Carlo; MENEGON, Sergio; TAZZARI, Valerio; (98 pag.)WO2019/145214; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-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. COA of Formula: C10H15BrN4O2

EXAMPLE 176; 7- {5- [(6,7-dichloro- 1-oxo- 1 ,2-dihydr opyr rolo [1 ,2-alphal pyrazin-4-yl)methyll -2- fluorobenzoyl}-3-pyrrolidin- l-yl-5,6,7,8-tetr ahydro [ 1 ,2,41 triazolo [4,3-alphal pyrazin-2-ium trifluoroacetate (AA2)Step 1: 3-Pyrrolidin-l-yl-5,6,7,8-tetrahydro[l,2,41triazolo[4,3-alphalpyrazin-7-ium trifluoroacetate (AAl)A mixture of tert-bvXy 3-bromo-5,6-dihydro[l,2,4]triazolo[4,3-alpha]pyrazine-7(8H)-carboxylate(0.231 mmol) in pyrrolidine (3 ml) was stirred overnight in a sealed tube at 6O0C. The volatiles were removed under reduced pressure and the resulting crude was diluted with DCM and washed with sat. aq. NH4Cl solution. The organic phase was dried (Na2SO4) and filtered. Evaporation of the solvent provided a crude which was dissolved in a mixture of DCM/TFA (1:1, 0.23 M) and stirred at room temperature for 30 min. The volatiles were removed under reduced pressure and the resulting crude was used as such in the next step without purification. MS (ES) C9H15N5 required: 193, found: 194 (M+H)+.

The synthetic route of tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2007/138355; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem