1,2-Dimethoxyethane → 1-(1,1-Dimethylethyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-6-[6-(4-methyl-1-piperazinyl)-3-pyridinyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Participants

Reaction Steps

The title compound was prepared in the same manner as described in example 74 using 6-chloro-1-(1,1-dimethylethyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.174 mmol), 1-methyl-4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]piperazine (68.7 mg, 0.226 mmol), DME (3 mL), water (1.00 mL), sodium carbonate (0.261 mL, 0.523 mmol) and PdCl2(dppf)-CH2Cl2 adduct (11.38 mg, 0.014 mmol), wherein the reaction time was 40 min. The crude product was purified by column chromatography (eluent: gradient of 0 to 15% (9:1 MeOH/NH4OH)/DCM). The final product was collected as a solid, 41 mg (43%). LCMS E-S (M+H)=543.2 1H NMR (400 MHz, DMSO-d6) δ ppm 1.78 (s, 9 H), 2.12 (s, 3 H), 2.24 (m, 7 H), 2.38 (s, 3 H), 2.39-2.49 (m, 4 H), 3.34 (s, 3 H), 4.38 (m, 2 H), 5.88 (s, 1 H), 6.98 (d, J=9.09 Hz, 1 H), 7.59 (s, 1 H), 8.93-8.97 (m, 1 H), 11.49-11.57 (m, 1 H), 11.53 (s, 1 H), 11.53 (s, 1 H).

Provenance & Evidence