4-(N-Boc-amino)piperidine → tert-butyl (1-(4-(5-(dimethylcarbamoyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrimidin-2-yl)piperidin-4-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(2-chloropyrimidin-4-yl)-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide (0.5 g, 1.29 mmol) in DMSO (5 mL) was added tert-butyl piperidin-4-ylcarbamate (0.311 g, 1.54 mmol) and the reaction was stirred for 12 h at 100° C. The reaction was quenched with ice cold water (5 mL) to give the off white precipitate. The suspension was filtered, washed with ice cold water and dried to give tert-butyl (1-(4-(5-(dimethylcarbamoyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrimidin-2-yl)piperidin-4-yl)carbamate (0.4 g, 48%) as a off white solid. MS (ESI, pos. ion) m/z: 550.3 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 8.54 (s, 1H), 8.45 (d, 1 H, J=5.1 Hz), 7.90 (d, 1 H, J=8.8 Hz), 7.35-7.65 (m, 1H), 7.28 (d, 1 H, J=5.1 Hz), 6.89 (d, 1 H, J=7.7 Hz), 6.01 (dd, 1 H, J=7.4, 2.0 Hz), 4.64 (d, 2 H, J=12.9 Hz), 3.90-4.04 (m, 1H), 3.76-3.82 (m, 1H), 3.60 (s, 1H), 3.16 (t, 2 H, J=11.8 Hz), 3.02 (s, 6H), 2.03-2.06 (m, 2H), 1.82-1.86 (m, 3H), 1.62 (bs, 2H), 1.23 (m, 12H).

Provenance & Evidence