HCID 178501052, compound → HCID 178501050, compound

Participants

Reaction Steps

A solution of trans-4-[8-Amino-1-(3-benzyloxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexanecarboxylic acid methyl ester (50 mg, 0.110 mmol) in 4M HCl in dioxane (2 mL) was heated to 75° C. in a oil-bath for ˜2 h. The reaction mixture was allowed to cool to rt, the dioxane was decanted off and the reaction mixture was quenched with 7N NH3 in MeOH solution (˜2 mL). This crude mixture was concentrated in vacuo resulting in 79 mg of an off-white solid (containing NH4Cl salts). The crude material was purified by flash silica chromatography (10% 7N NH3 in MeOH in CHCl3) resulting in an off-white solid; 1H NMR (DMSO-d6, 400 MHz) δ 1.51-1.78 (m, 4H), 1.95-2.08 (m, 4H), 2.38-2.48 (m, 1H), 3.07-3.20 (m, 1H), 3.63 (s, 3H), 6.06 (brs, 2H), 6.76-6.89 (m, 1H), 6.95-7.05 (m, 3H), 7.29 (t, 1H, J=7.8 Hz), 7.65 (d, 1H, J=5.1 Hz), 9.62 (brs, 1H); MS (ES+): m/z 367.26 [MH+].

Provenance & Evidence