Tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate → 1-(1,3-Dimethyl-1h-pyrazol-4-yl)-3-methyl-8-(6-piperazin-1-yl-pyridin-3-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Participants

Reaction Steps

The title compound was synthesized in a similar manner as described for Example 118.1 using 8-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A) and 2-(4-boc-piperazine)pyridine-5-boronic acid pinacol ester (Combi-Blocks, San Diego, USA) to give the title compound as a white solid. (HPLC: tR 1.97 min (Method A); M+H=455 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.91 (s, 1H), 8.30-8.25 (m, 1H), 8.14-8.11 (m, 1H), 8.07-8.01 (m, 1H), 7.90-7.84 (m, 1H), 7.62-7.56 (m, 1H), 7.46-7.41 (m, 1H), 6.95-6.89 (m, 1H), 3.92 (s, 3H), 3.57 (s, 3H), 3.53-3.46 (m, 4H), 2.86-2.76 (m, 4H), 1.95 (s, 3H))

Provenance & Evidence