Some common heterocyclic compound, 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine, molecular formula is C6H9N3, 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 297172-19-1
To a solution of 2-bromo-N-[1-(1 H-indol-3-ylmethyl)pentyl]thiazole-5- carboxamide (0.40 g, 0.98 mmol) and 5,6,7,8-tetrahydroimidazo[1 ,5-a]pyrazine (0.18 g, 1.48 mmol) in dioxane (16 ml_), Cs2C03 (0.96 g, 2.96 mmol) and RuPhos (0.09 g, 0.19 mmol) were added and the reaction mixture was purged with argon for 30 min. Pd2(dba)3 (0.09 g, 0.09 mmol) was added and the reaction mixture was heated in sealed tube at 1 10C for 16h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was diluted with H20 (100 ml.) and extracted with EtOAc (3 * 100 ml_). The organic layer was separated, washed with brine (100 ml_), dried over anhydrous Na2SC>4 and concentrated in vacuo. The crude residue obtained was purified by column chromatography (silica, 100-200 mesh, 0 to 5% MeOH in DCM) and by preparative HPLC to afford 2-(6,8-dihydro-5H-imidazo[1 ,5- a]pyrazin-7-yl)-N-[1-(1 H-indol-3-ylmethyl)pentyl]thiazole-5-carboxamide (0.07 g, 14%) as a white solid. HPLC Purity: 98.3% MS (ESI) m/e [M+H]7Rt/%: 449.00/2.76/96.0% 1H NMR (400 MHz, DMSO-d6) delta 0.81 (t, J=6.60 Hz, 3H) 1.18 – 1.35 (m, 4H) 1.44 – 1.60 (m, 2H) 2.82 – 2.92 (m, 2H) 3.89 (t, J=5.38 Hz, 2H) 4.1 1 (d, J=4.40 Hz, 1 H) 4.19 (t, J=5.38 Hz, 2H) 4.71 (s, 2H) 6.83 (s, 1 H) 6.93 – 6.98 (m, 1 H) 7.04 (t, J=7.34 Hz, 1 H) 7.10 (d, J=1.47 Hz, 1 H) 7.31 (d, J=7.82 Hz, 1 H) 7.57 (d, J=7.82 Hz, 1 H) 7.65 (s, 1 H) 7.87 (s, 1 H) 8.01 (d, J=8.80 Hz, 1 H) 10.76 (brs, 1 H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 297172-19-1, its application will become more common.
Reference:
Patent; UCB BIOPHARMA SPRL; HALL, Adrian; PROVINS, Laurent; MACCOSS, Malcolm; (72 pag.)WO2018/138088; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem