1,4-Dioxane → 6-{3-[(dimethylamino)methyl]phenyl}-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide hydrochloride salt

Participants

Reaction Steps

The title compound was prepared in the same manner as described for example 33 using from 6-bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide (200 mg, 0.449 mmol), 3-(N,N dimethylaminomethyl)phenylboronic acid pinacol ester hydrochloride (170 mg, 0.571 mmol), potassium phosphate (300 mg, 1.413 mmol), dioxane (12 mL), water (3 mL), and PdCl2(dppf)-CH2Cl2 adduct (50 mg, 0.061 mmol). The product was obtained as a light tan solid (204 mg, 85% yield). 1H NMR (400 MHz, DMSO-d6) δ=11.67 (br. s., 1H), 10.97 (br. s., 1H), 8.68 (t, J=5.1 Hz, 1H), 8.38 (s, 1H), 8.30 (s, 1H), 8.16 (s, 1H), 8.00-7.94 (m, 1H), 7.92 (d, J=1.0 Hz, 1H), 7.65-7.53 (m, 2H), 5.96 (s, 1H), 5.18 (dt, J=6.6, 13.3 Hz, 1H), 4.43 (d, J=5.1 Hz, 2H), 4.38 (d, J=5.6 Hz, 2H), 2.74 (d, J=4.8 Hz, 6H), 2.61-2.52 (m, 2H), 2.15 (s, 3H), 1.59-1.52 (m, 2H), 1.51 (d, J=6.6 Hz, 6H), 0.90 (t, J=7.3 Hz, 3H); LC-MS (ES)+ m/e 500.2 [M+H]+.

Provenance & Evidence