p-Toluenesulfonic acid → HCID 90005004, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Intermediate E3 (1.50 g, 5.50 mmol), 1H-indazol-5-amine (735 mg, 5.52 mmol) and p-TSA (525 mg, 2.76 mmol) in DMF (14.0 mL) was degassed with nitrogen and was then heated to 60° C. for 16 hr. Additional p-TSA (525 mg, 2.76 mmol) and 1H-indazol-5-amine (368 mg, 2.76 mmol) was added and the reaction maintained at 60° C. for a further 3 hr and then cooled to RT. The resulting mixture was diluted with EtOAc (250 mL) and was washed sequentially with saturated aq. NaHCO3 (2×50 mL), water (2×50 mL) and brine (2×50 mL) and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 120 g, 0-10% [1% NH3 in MeOH] in DCM, gradient elution) to afford the title compound, Intermediate B14, as a dark purple solid (536 mg, 26%); Rt 1.59 min (Method 2, acidic); m/z 369 (M+H)+, (ES+).

Provenance & Evidence