Diisopropylethylamine → N-(2-methyl-1,3-benzothiazol-5-yl)-2-((1H-pyrazolo[3,4-b]pyridin-4-ylmethyl)amino)-3-pyridinecarboxamide

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-N-(2-methyl-benzothiazol-5-yl)-nicotinamide (100 mg, 0.348 mmol) was dissolved in NMP (0.5 mL), then C-(1H-pyrazolo[3,4-b]pyridin-4-yl)-methylamine (52 mg, 0.348 mmol) and DIEA (91 μL, 0.522 mmol) were added. The reaction was heated at 120° C. for 20 h. Additional C-(1H-pyrazolo[3,4-b]pyridin-4-yl)-methylamine (25 mg, 0.174 mmol) and DIEA (91 μL, 0.522 mmol) were added and the mixture was heated at 120° C. for another 23 h. The mixture was partitioned between H2O and EtOAc then extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4. Purification was achieved by preparative TLC (10% MeOH/CH2Cl2), followed by trituration with CH2Cl2 to give N-(2-methyl-1,3-benzothiazol-5-yl)-2-((1H-pyrazolo[3,4-b]pyridin-4-ylmethyl)amino)-3-pyridinecarboxamide as a light yellow solid. MS m/e 416.0 (M+H)+. Calc'd for C21H17N7O—415.48.

Provenance & Evidence