Cyclopentylamine → ethyl 4-(cyclopentylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

Intermediate 1 (0.051 g) and cyclopentyl amine (0.019 g) were suspended in ethanol (2 ml) and triethylamine (0.14 ml) was added. The mixture was stirred under nitrogen and heated at 80° C. for 16 h. After cooling to room temperature, ethanol was removed by evaporation under a stream of nitrogen and the residue partitioned between DCM and water. The organic layer was loaded directly onto an SPE cartridge (silica, 5 g) and eluted sequentially with; (i) DCM, (ii) DCM:Et2O (2:1), (iii) DCM:Et2O (1:1), (iv) Et2O, (v) EtOAc and (vi) MeOH. Fractions containing desired material were combined and concentrated in vacuo to afford Intermediate 2 (0.074 g). LCMS showed MH+303; TRET=3.45 min

Provenance & Evidence