These common heterocyclic compound, 297172-19-1, name is 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine, 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. Computed Properties of C6H9N3
Example 94 N-(5-(5,6-dihydroimidazo[1,5-a]pyrazin-7(8H)-yl)pentyl)-5-(thiophen-2-yl)isoxazole-3-carboxamide To a solution of intermediate B (150 mg, 0.54 mmol, 1.0 eq) in CH2ClCH2Cl (10 mL) were added imidazo[1,5-a]pyrazine,5,6,7,8-tetrahydro-(9Cl) (132.7 g, 1.07 mmol, 2.0 eq), NaBH(OAc)3 (685.3 mg, 3.24 mmol, 6.0 eq), acetic acid (97.1 mg, 1.62 mmol, 3.0 eq). Then the mixture was stirred at 15 C. for 12 hours. The mixture was quenched with water (10 mL). The mixture was extracted with DCM. The combined organic phase was concentrated to obtain the crude product which was purified by preparative HPLC (column: Xtimate C18 150*25 mm*5 um, gradient: 33-63% B (A=0.05% ammonia hydroxide/water, B=acetonitrile) to give the title compound (95 mg, 45.7% yield) as a light yellow solid. MS (ESI) m/z 386.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 8.80 (t, J=5.6 Hz, 1H), 7.86 (dd, J=5.2, 0.8 Hz, 1H), 7.78 (dd, J=4.0, 1.2 Hz, 1H), 7.49 (s, 1H), 7.27-7.25 (m, 1H), 7.16 (s, 1H), 6.61 (s, 1H), 3.97 (t, J=5.6 Hz, 2H), 3.53 (s, 2H), 3.28-3.23 (m, 2H), 2.73 (t, J=5.6 Hz, 2H), 2.45 (t, J=6.8 Hz, 2H), 1.58-1.48 (m, 4H), 1.36-1.30 (m, 2H).
The synthetic route of 5,6,7,8-Tetrahydroimidazo[1,5-a]pyrazine has been constantly updated, and we look forward to future research findings.
Reference:
Patent; NOVARTIS AG; BECKWITH, Rohan Eric John; JIANG, Hua; WANG, Ce; (54 pag.)US2018/271837; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem