1,1'-Carbonyldiimidazole → (8aS)-1,3-dioxo-2-[(1S,2R)-2-phenylcyclopropyl]-N-(1-phenyl-1H-pyrazol-5-yl)hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxamide

Participants

Reaction Conditions

Reaction Steps

F1 (1.0 eq.) was dissolved in MeCN (0.1M) and CDI (1.0 eq.) was added. The reaction was stirred at 80° C. for 5 h. After cooling at RT a solution of (D2) (0.5 eq.) and TEA (0.6 eq.) in MeCN (0.2M) was added dropwise. The mixture was stirred overnight. The solvents were removed under reduced pressure. Crude product was purified by preparative RP-HPLC using H2O (0.1% TFA) and MeCN (0.1% TFA) as eluents. The desired fractions were lyophilized to afford the title compound in 33% yield. 1H NMR (400 MHz, DMSO-d6, 300K) δ 8.91 (1H, s), 7.62 (1H, d, J=1.7 Hz), 7.54-7.47 (4H, m), 7.37 (1H, m), 7.30 (2H, m), 7.22-7.20 (3H, m), 6.31 (1H, d, J=1.7 Hz), 4.24 (1H, m), 4.02-3.96 (2H, m), 3.87 (1H, m), 2.97 (1H, m), 2.84 (2H, m), 2.67 (1H, m), 2.38 (1H, m), 1.52-1.48 (1H, m), 1.40 (1H, m). MS (ES+) C25H24N6O3 requires 456, found: 457 (M+H+).

Provenance & Evidence