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