1,2-Dichloroethane → 1-Amino-6-cyclopropyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Participants

Reaction Steps

The title compound was prepared in the same manner as described for intermediate 56 using 1-amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (73 mg, 0.335 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (76 mg, 0.502 mmol), 1-hydroxy-7-azabenzotriazole (91 mg, 0.669 mmol), DMSO (10 mL), EDC (128 mg, 0.669 mmol), and N-methylmorpholine (0.147 mL, 1.338 mmol). The aq. phase was extracted with EtOAc (5×30 mL). The combined EtOAc extracts were dried over MgSO4, filtered, and concentrated in vacuo. The final product was collected as 0.068 g (58%). LCMS E-S (M+H)=353.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99-1.14 (m, 4H), 2.13 (s, 3H), 2.22 (s, 4H), 4.35 (d, J=4.80 Hz, 2H), 5.90 (s, 1H), 6.31 (s, 2H), 7.41 (s, 1H), 8.04 (s, 1H), 8.74 (s, 1H), 11.58 (br. s., 1H).

Provenance & Evidence