Trifluoroacetic acid → HCID 59437059, compound

Participants

Reaction Steps

To a solution of 2-amino-N-[5-(3,5-difluoro-benzenesulfonyl)-1-trityl-1H-indazol-3-yl]-4-[(2-dimethylamino-ethyl)-methyl-amino]-benzamide (400 mg, 0.52 mmol) in dichloromethane (5 mL) were added tetrahydro-pyran-4-one (0.071 mL, 0.78 mmol), trifluoroacetic acid (0.108 mL, 1.4 mmol) and tetramethylammonium triacetoxyborohydride (205 mg, 0.78 mmol). The mixture was stirred at room temperature overnight, then additional trifluoroacetic acid (0.8 mL) and tetramethylammonium triacetoxyborohydride (410 mg) were added. After stirring for additional 3 hours at room temperature the mixture was diluted with dichloromethane, washed with saturated solution of sodium hydrogenocarbonate, brine, dried over sodium sulfate and evaporated to dryness. The crude was purified by flash chromatography on silica gel using dichloromethane/methanol/NH4OH 96:4:0.5 as the eluant, affording 175 mg of the title compound as a pale yellow solid.

Provenance & Evidence