Reaction Steps
To a solution of (R)-6-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (0.062 g, 0.089 mmol) in DCM (2 mL) under an atmosphere of nitrogen was added N-chlorosuccinimide (0.012 g, 0.089 mmol). The mixture was left to stir for 1 h at rt. The reaction mixture was then directly purified by FCC (40-75% EtOAc/heptanes) to give the title compound. 1H NMR (400 MHz, DICHLOROMETHANE-d2) δ ppm 8.08 (d, J=8.3 Hz, 1 H), 7.79 (d, J=8.3 Hz, 2 H), 7.45 (d, J=8.8 Hz, 1 H), 7.25 (d, J=8.3 Hz, 2 H), 4.32 (d, J=14.7 Hz, 1 H), 4.22 (d, J=14.4 Hz, 1 H), 3.67 (d, J=11.6 Hz, 1 H), 3.58 (s, 3 H), 3.52 (dq, J=12.8, 6.3 Hz, 2 H), 3.28-3.36 (m, 4 H), 3.09 (br. s., 1 H), 2.99 (br. s., 2 H), 2.92 (dd, J=8.6, 3.8 Hz, 1 H), 2.86 (d, J=11.6 Hz, 1 H), 2.72 (s, 2 H), 2.36 (s, 3 H), 2.25 (s, 3 H), 1.88-1.96 (m, 4 H), 1.78-1.88 (m, 1 H), 1.52-1.69 (m, 3 H), 0.94 (s, 3 H), 0.81-0.90 (m, 8 H); MS (ESI+) m/z 729.4 (M+H)+.
