Cesium carbonate → 6-{[4-(Aminocarbonyl)phenyl]amino}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-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-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.180 mmol), 4-aminobenzamide (29.5 mg, 0.217 mmol), cesium carbonate (88 mg, 0.271 mmol), N,N-dimethylacetamide (DMA) (1.5 mL), palladium(II) acetate (2.431 mg, 10.83 μmmol) and Xantphos (10.44 mg, 0.018 mmol) wherein the reaction temperature was 150° C. and reaction time was 1 h. The final product was collected as 12 mg (14%). LCMS E-S (M+H)=488.2 1H NMR (400 MHz, DMSO-d6) δ ppm 1.48 (d, J=6.4 Hz, 6 H), 2.13 (s, 3 H), 2.23 (s, 3 H), 2.32 (s, 3 H), 4.35 (d, J=4.8 Hz, 2 H), 4.99 (quin, J=6.8 Hz, 1 H), 5.89 (s, 1 H), 6.65 (s, 1 H), 7.15 (br. s., 1 H), 7.75-7.82 (m, 1 H), 7.84-7.96 (m, 4 H), 8.56 (t, J=4.9 Hz, 1 H), 9.77 (s, 1 H).

Provenance & Evidence