Hydrazine → HCID 11338529, compound

Participants

Reaction Steps

2-{3-[3-(8-Amino-3-cyclobutyl-imidazo[1,5-a]pyrazin-1-yl)-phenoxymethyl]-benzyl}-isoindole-1,3-dione (100 mg, 0.19 mmol) was dissolved in EtOH (0.76 mL) and charged with hydrazine (60 mg, 1.89 mmol) and stirred overnight at rt. The white ppt filtered and washed with EtOH. The filtrate was concentrated in vacuo, silica gel was added in CH2Cl2, and concentrated to solid. The product was chromatographed on silica gel [Jones Flashmaster, 2 g cartridge, eluting with ˜2% 7N NH3 MeOH:CH2Cl2] and isolated the title compound as a yellow solid; 1H NMR (CDCl3, 400 MHz) δ 1.84-1.92 (m, 1H), 1.97-2.09 (m, 1H), 2.34-2.40 (m, 2H), 2.44-2.46 (m, 2H), 3.69 (s, 2H), 3.84-3.92 (m, 1H), 5.10 (s, 2H), 6.96 (d, J=5.2 Hz, 1H), 7.01-7.03 (m, 1H), 7.13-7.16 (m, 1H), 7.18-7.19 (m, 1H), 7.23-7.32 (m, 3H), 7.35-7.40 (m, 3H); MS (ES+): m/z 400.17 (100) [MH+].

Provenance & Evidence