Ammonia → HCID 11293122, compound

Participants

Reaction Conditions

Reaction Steps

Gaseous NH3 was condensed into a cooled (−78° C.) solution of {3-[1-(3-benzyloxyphenyl)-8-chloroimidazo[1,5-a]pyrazin-3-yl]-phenyl}-methanol (366 mg, 0.829 mmol) in NH3/i-PrOH (2M, 5 mL) in a pressure tube until the volume had doubled. The tube was sealed and heated to 110° C. for 19 h. After excess NH3/i-PrOH was removed in vacuo, the residue was suspended between CH2Cl2 and water, the layers were separated, and the aqueous layer was extracted with CH2Cl2 (3×30 mL). The combined organic layers were washed with brine (3×30 mL), dried over anhydrous MgSO4, and filtered. The crude material was purified by filtration through a plug of silica gel, eluting with 5% MeOH:CH2Cl2 (400 mL), concentrated in vacuo, giving 311.5 mg (89%, 0.737 mmol) of the title compound, as a yellow solid; 1H NMR (CDCl3, 400 MHz) δ 4.80 (s, 2H), 5.09 (s, —NH2), 5.16 (s, 2H), 7.05-7.09 (m, 1H), 7.11 (d, J=4.8 Hz, 1H), 7.29-7.37 (m, 3H), 7.37-7.48 (m, 5H), 7.47-7.51 (m, 1H), 7.54 (t, J=7.8 Hz, 1H), 7.63 (d, J=4.8 Hz, 1H), 7.73-7.78 (m, 1H), 7.86 (s, 1H); MS (ES+): m/z 423.0 (100) [MH+].

Provenance & Evidence