Category: 233278-56-3

Application of 233278-56-3, 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. 233278-56-3, name is 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 4 5-[5,6-Dihydro[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl]-3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazoline Prepared from 5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazine as described for Example 1, step c (0.047 g, 53%). Found: C, 62.52; H, 3.96; N, 29.10. C20H15FN8 requires C, 62.17; H, 3.91; N, 29.00%. deltaH (360 MHz; CDCl3) 4.16 (2H, dd, J=5 and 5), 4.61 (2H, dd, J=5 and 5), 5.02 (2H, s), 7.22-7.33 (2H, m), 7.40-7.42 (1H, m), 7.71 (1H, dd, J=8 and 8), 7.95-8.08 (4H, m), 8.75 (1H, d, J=8); m/z (ES+) 387 (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, 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chambers, Mark Stuart; Collins, Ian James; Goodacre, Simon Charles; Hallett, David James; Jones, Philip; Keown, Linda Elizabeth; Maxey, Robert James; Street, Leslie Joseph; US2003/45532; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 233278-56-3, 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 233278-56-3 as follows.

Step 1: tert-Butyl 9-(5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-3-azaspiro[5.5]undecane-3-carboxylate Acetic acid (2.34 eq.) was added to a solution of tert-butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (1.122 mmol, 1 eq.) and 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine (1.14 eq.) in methylene chloride (7 ml). Sodium triacetoxyborhydride (1.4 eq) was then added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with methylene chloride and sat. NaHCO3 solution. The aqueous phase was washed with methylene chloride (2*20 ml), and the combined organic phases were dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography (silica, ethyl acetate/ethanol 10:1) to obtain the desired product. Yield: 62%

According to the analysis of related databases, 233278-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gruenenthal GmbH; US2010/249095; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 233278-56-3, A common heterocyclic compound, 233278-56-3, name is 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine, molecular formula is C5H8N4, 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.

Parallel preparation of Examples 165-195: To a set of vials containing the chloropyrimidine core from Scheme H (25 mg, 0.056 mmol) in DMSO (0.3 mL) was individually added the requisite amine (0.067 mmol) and diisopropylethylamine (0.039 mL, 0.223 mmol). The vials were capped and the mixtures were heated to 1 10C with stirring for 3 hours. The mixtures were cooled to RT. Water (2 mL) was added to each vial. The aqueous phase from each vial was extracted with DCM (2 x 1 mL). The organic layers from each vial were transferred to a clean vial and the solvent was removed in vacuo. To each vial was then added THF:MeOH (1 :3, 1 mL) followed by HCI (4 N in dioxane, 0.20 mL, 0.80 mmol). The vials were capped and the solutions were heated to 70C for 0.5 h. The solutions were allowed to cool to RT and the solvent was then removed from the vials in vacuo. Each crude product was redissolved in 1 mL of DMSO and filtered. The crude products (excluding Example 195) were purified by mass triggered HPLC using the following conditions: [Waters XBridge CI 8 column, 5muiotaeta, 19×100 mm, gradient ranges from 10 initial to 60-70% MeCN (0.1% NH4OH) in water (0.1% NH4OH) 25 mL/min, 8 min run time] to provide the Examplesl65-190. Examples 191-194 were repurified using the following conditions: [Waters Sunfire CI 8 column, 5muetaiota, 19×100 mm, gradient ranges of 10% initial to 70-95% MeCN (0.1% TFA) in water (0.1% TFA) 25 mL/min, 8 min run time]. Example 195 was purified using the following condition: [Waters Sunfire CI 8 column, 5muetaalpha, 19×100 mm, gradient 10% to 50% MeCN (0.1% formic acid) in water (0.1 % formic acid) 25 mL/min, 8 min run time]. Table 11: Parallel preparation of Examples 165-195.

The synthetic route of 233278-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MILLER, Michael; BASU, Kallol; DEMONG, Duane; SCOTT, Jack; LI, Wei; STAMFORD, Andrew; POIRIER, Marc; TEMPEST, Paul; WO2014/137723; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 233278-56-3, The chemical industry reduces the impact on the environment during synthesis 233278-56-3, name is 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine, I believe this compound will play a more active role in future production and life.

Example 16 4-[[3-(6,8-dihydro-5H-[1,2,4]triazolo[1,5-a]pyrazine-7-carbonyl)-4-fluoro-phenyl]methyl]-2H-phthalazin-1-one 2-Fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoic acid 1a (360 mg, 1.20 mmol) was dissolved in 10 mL of N,N-dimethylformamide, followed by addition of O-(1-benzotriazolyl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (600 mg, 1.80 mmol), 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine 16a (150 mg, 1.20 mmol, prepared according to a known method disclosed by “patent application WO2009090055”) and N,N-diisopropylethylamine (0.4 mL, 2.40 mmol). After stirring for 20 hours, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by thin layer chromatography with elution system A to obtain 4-[[3-(6,8-dihydro-5H-[1,2,4]triazolo[1,5-a]pyrazine-7-carbonyl)-4-fluoro-phenyl]methyl]-2H-phthalazin-1-one 16 (100 mg, yield 21.0%) as a yellow solid. MS m/z (ESI): 405.1 [M+1] 1H NMR (400 MHz, CDCl3): delta 10.47 (br. s, 1H), 8.51-8.49 (m, 1H), 7.99-1.77 (m, 4H), 7.42-7.30 (m, 2H), 7.30-7.12 (m, 1H), 4.76 (m, 2H), 4.37-4.28 (m, 4H), 3.77-3.73 (m, 2H)

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, 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference of 233278-56-3, The chemical industry reduces the impact on the environment during synthesis 233278-56-3, name is 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine, I believe this compound will play a more active role in future production and life.

Description 35: 3-(5,6-Dihydro[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-ylmethyl)-2-phenylquinoline-4-carboxylic Acid A mixture of 3-(bromomethyl)-2-phenylquinoline-4-carboxylic acid (Description 5, 3.4 g, 10.3 mmol), 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine (1.24 g, 9.1 mmol) and triethylamine (1.39 mL, 1.01 g, 10 mmol) in DMF (50 mL) was heated at 60 C. for 40 h. The mixture was cooled and the solvent was evaporated under reduced pressure. EtOAc (500 mL) was added and the mixture was heated to reflux, filtered and cooled. The solvent was evaporated under reduced pressure to a volume of 100 mL and the solid was collected and dried in vacuo to give the title compound as a solid (1.0 g, 28%). m/z (ES+) 386 [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, 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 233278-56-3, 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. 233278-56-3, name is 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-bromo-N-[1-(1 H-indol-3-ylmethyl)pentyl]thiazole-5- carboxamide (0.20 g, 0.49 mmol) and 5,6,7,8-tetrahydro-[1 ,2,4]triazolo[1 ,5- a]pyrazine (0.07 g, 0.59 mmol) in dioxane (5 ml_), CS2CO3 (0.24 g, 0.73 mmol) and RuPhos (0.05 g, 0.10 mmol) was added. The reaction mixture was purged with argon for 20 min followed by addition of Pd2(dba)3 (0.05 g, 0.05 mmol) and again purged with argon for 20 min. The reaction mixture was heated at 100C for 3h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was filtered through Celite, washed with 5% MeOH in DCM (30 ml_). The organic layer was separated, washed with H2O15 ml_), brine (15 ml_), dried over anhydrous Na2SC>4 and concentrated in vacuo. The crude residue obtained was purified by column chromatography (silica, 100-200 mesh, 1 to 4% MeOH in DCM) and prep HPLC to afford 2-(6,8- dihydro-5H-[1 ,2,4]triazolo[1 ,5-a]pyrazin-7-yl)-N-[1-(1 H-indol-3- ylmethyl)pentyl]thiazole-5-carboxamide (0.04 g, 18%) as off-white solid.HPLC Purity: 99.4%MS (ESI) m/e [M+H]7Rt/%: 450.00/2.58/97.4% 1H NMR (400 MHz, DMSO-d6) delta 0.82 (t, J=6.85 Hz, 3H) 1.12 – 1.36 (m, 4H) 1.42 – 1.65 (m, 2H) 2.82-2.94 (m, 2H) 3.99 – 4.18 (m, 3H) 4.30 (t, J=5.14 Hz, 2H) 4.81 (s, 2H) 6.93 – 6.99 (m, 1 H) 7.04 (t, J=7.58 Hz, 1 H) 7.10 (s, 1 H) 7.31 (d, J=8.31 Hz, 1 H) 7.57 (d, J=7.82 Hz, 1 H) 7.88 (s, 1 H) 8.01 (s, 1 H) 8.06 (d, J=8.80 Hz, 1 H) 10.76 (brs, 1 H).

The synthetic route of 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; HALL, Adrian; PROVINS, Laurent; MACCOSS, Malcolm; (72 pag.)WO2018/138088; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

233278-56-3, name is 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine

To a solution of (S)-N-((3 -(4-bromophenyl)-2-oxooxazolidin-5 – yl)methyl)acetamide (100.0 mg, 0.319 mmol), 5 ,6,7,8-tetrahydro-[ 1 ,2,4]triazolo[ 1 ,5-a]pyrazine (150.0 mg, 1.208 mmol) and Cs2CO3 (312.0 mg, 0.958 mmol) in 1,4-Dioxane (2 mL) was added 2nd generation ruphos precatalyst (12.4 mg, 0.0 16 mmol) under N2 atmosphere. The mixturewas stirred at 100C for 16 hours. The reaction mixture was concentrated to give a residuewhich was purified by reverse phase prep-HPLC to give (S)-N-((3-(4-(5,6-dihydro-[1,2 ,4]triazolo[ 1,5 -a]pyrazin-7(8H)-yl)phenyl)-2-oxooxazolidin-5 -yl)methyl)acetamide as solid. MS(ESI) m/z: 357.1 [M+Hj.

The synthetic route of 233278-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; YANG, Lihu; OLSEN, David B.; YOUNG, Katherine; SU, Jing; MANDAL, Mihir B.; SUZUKI, Takao; YOU, Lanying; (85 pag.)WO2017/66964; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem