1-Methyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine → 3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-[6-(4-methyl-1-piperazinyl)-3-pyridinyl]-1H-indazole-4-carboxamide

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The title compound was prepared in the same manner as described for example 67 from 6-bromo-3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide (0.10 g, 0.218 mmol) and 1-methyl-4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]piperazine (0.086 g, 0.283 mmol). The title compound was collected as a white solid (0.105 g, 84%); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92 (t, J=7.33 Hz, 3H), 1.45 (d, J=6.57 Hz, 6H), 1.50-1.63 (m, 2H), 2.12 (s, 3H), 2.22 (s, 3H), 2.38-2.45 (m, 7H), 2.52-2.59 (m, 2H), 3.51-3.60 (m, 4H), 4.37 (d, J=5.05 Hz, 2H), 4.96-5.10 (m, 1H), 5.90 (s, 1H), 6.94 (d, J=8.84 Hz, 1H), 7.32 (d, J=1.26 Hz, 1H), 7.89 (d, J=1.26 Hz, 1H), 7.98 (dd, J=8.84, 2.53 Hz, 1H), 8.40 (t, J=5.05 Hz, 1H), 8.56 (d, J=2.27 Hz, 1H), 11.50 (s, 1H); LCMS (ES+) m/z: 556.1.

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