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

Participants

Reaction Steps

Following the procedures as described in Example 189, 3-(6-fluoropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine and (S)-tert-butyl piperidin-3-ylcarbamate were reacted and the product was deprotected to give 173 as a white solid (71.7% over two steps). 1H NMR (400 MHz, DMSO) δ 1H NMR (400 MHz, DMSO) δ 9.03 (d, J=1.2 Hz, 1H), 8.59 (d, J=1.2 Hz, 1H), 8.34 (s, 1H), 7.95 (s, 1H), 7.67-7.60 (m, 1H), 7.42 (d, J=7.3 Hz, 1H), 6.84 (d, J=8.5 Hz, 1H), 4.46 (d, J=8.9 Hz, 1H), 4.21 (d, J=12.7 Hz, 1H), 3.90 (s, 3H), 3.02-2.93 (m, 1H), 2.84-2.74 (m, 2H), 2.00-1.92 (m, 2H), 1.88-1.77 (m, 2H), 1.67-1.52 (m, 2H), 1.39-1.28 (m, 1H). LC/MS: m/z 375.1 [M+1]

Provenance & Evidence