tert-butyl N-[(3S)-piperidin-3-yl]carbamate → (S)-3-(3-Aminopiperidin-1-yl)-1-methyl-5-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyrazin-2(1H)-one

Participants

Reaction Steps

Following the procedures as described in Example 124 and starting with (5)-tert-butyl piperidin-3-ylcarbamate, 3,5-dibromo-1-methylpyrazin-2(1H)-one, 6-chloro-1H-pyrazolo[4,3-c]pyridine, and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 242 was obtained as a yellow solid (60 mg, 18.1%) over four steps. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.09 (s, 1H), 8.45 (s, 1H), 8.37 (s, 1H), 8.32 (s, 1H), 8.00 (s, 1H), 7.64 (s, 1H), 4.59-4.72 (m, 2H), 3.91 (s, 3H), 3.51 (s, 3H), 2.98-3.04 (m, 1H), 2.83-2.92 (m, 1H), 2.80-2.81 (m, 1H), 1.92-1.94 (m, 1H), 1.78-1.79 (m, 1H), 1.61-1.62 (m, 1H), 1.28-1.34 (m, 1H); MS (ESI) m/z: 406 (M+H)+.

Provenance & Evidence