Hydrochloric Acid → HCID 57960940, compound

Participants

Reaction Steps

A mixture of 3-cyclobutyl-1-[4-(3-nitrophenoxy)-phenyl]-imidazo[1,5-a]pyrazin-8-ylamine (10 mg, 0.02 mmol), iron (10 mg, 0.2 mmol), EtOH (10 mL, 0.2 mol) and conc. HCl (100 uL, 0.003 mol) was refluxed for 1 h. Sat. NaHCO3 was added to quench, and the EtOH was removed in vacuo. The mixture was transferred to a separatory funnel, and DCM was used to extract the product. The organic layer was concentrated in vacuo, redissolved in minimal MeOH/DCM, and loaded onto a prep TLC plate. After eluting with 10% (7N NH3 in MeOH)/DCM, the band containing the pure product was collected, and the material filtered off using 1:1 MeOH/DCM. The filtrate was concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=2.00-2.08 (m, 1H) 2.13-2.24 (m, 1H) 2.44-2.55 (m, J=8.91, 8.75, 8.75, 2.91, 2.78 Hz, 2H) 2.64 (quin, J=9.28 Hz, 2H) 3.71 (br. s., 2H) 3.82 (dq, J=8.84, 8.59 Hz, 1H) 5.05 (br. s., 2H) 6.38 (t, J=2.15 Hz, 1H) 6.46 (dd, J=8.08, 1.26 Hz, 2H) 7.05-7.16 (m, 5H) 7.63 (d, J=8.59 Hz, 2H). MS (ES+): m/z 372.10 (20) [MH+]. HPLC: tR=2.22 min (Open Lynx, polar—5 min).

Provenance & Evidence