p-Toluenesulfonic acid → HCID 90004998, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Intermediate E2 (223 mg, 0.738 mmol), 3-(2-morpholinoethoxy)-1H-indazol-5-amine (215 mg, 0.738 mmol) and p-TSA (140 mg, 0.738 mmol) in a mixture of DMF and THF (1:1 v/v, 20 mL) was heated to 90° C. for 6 h and then cooled to RT and maintained at that temperature for a further 64 hr. The reaction mixture was partitioned between saturated aq. NaHCO3 (50 mL) and EtOAc (50 mL). The aq layer was separated and extracted with EtOAc (50 mL) and the combined organic extracts were dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, 0-10% [0.1% NH3 in MeOH] in DCM, gradient elution) to afford the title compound, Intermediate B17, as a black solid (201 mg, 49%); Rt 1.32 min (Method 2, acidic); m/z 498 (M+H)+ (ES+).

Provenance & Evidence