HCID 69309475, compound → HCID 69309582, compound

Participants

Reaction Conditions

Reaction Steps

4-{1-[2-(4-{[2-(t-Butyl-dimethyl-silanyloxy)-ethyl]-methanesulfonylamino}-cyclo-hexylamino)-pyrimidin-4-yl]-1H-indol-4-yl}-piperazin-1-carboxylic acid t-butyl ester (0.251 g, 0.345 mmol) and hexafluoroisopropanol (10 mL) were combined and heated to 150° C. for 2 h in a microwave oven. The solvent was removed in vacuo to yield crude 1-{1-[2-(4-{[2-(t-Butyl-dimethyl-silanyloxy)-ethyl]-methanesulfonylamino}-cyclohexylamino)-pyrimidin-4-yl]-1H-indol-4-yl}-piperazine (0.267 g). This intermediate (0.193 g) and acetic anhydride (0.03 mL) in NMP (0.3 mL) was allowed to stir at RT for 6 h. EtOAc and water were then added, the organic layer separated and the organic layers combined, washed with water, sat. NaHCO3, dried over sodium sulfate, filtered, the solvent removed in vacuo, and the product purified on a silica column eluting with 0% to 10% MeOH/EtOAc to yield 1-{1-[2-(4-{[2-(t-butyl-dimethyl-silanyloxy)-ethyl]-methanesulfonylamino}-cyclohexylamino)-pyrimidin-4-yl]-1H-indol-4-yl}-4-acetyl-piperazine (0.119 g, 58%).

Provenance & Evidence