1-Methylpiperazin-2-one → 1-methyl-4-{3-[6-(piperazin-1-yl)pyridin-2-yl]-1H-pyrazolo[3,4-c]pyridin-5-yl}piperazin-2-one
Reaktionsgleichung
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([N:17]4[CH2:22]CC[C@H:19]([NH:23][C:24](=O)OC(C)(C)C)[CH2:18]4)[CH:14]=[CH:13][CH:12]=3)=[N:9][N:8](C3CCCCO3)[C:5]2=[CH:6][N:7]=1.[CH3:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][C:39]1=[O:44]>>[CH3:37][N:38]1[CH2:43][CH2:42][N:41]([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[CH:12]=[CH:13][CH:14]=[C:15]([N:17]5[CH2:22][CH2:24][NH:23][CH2:19][CH2:18]5)[N:16]=4)=[N:9][NH:8][C:5]3=[CH:6][N:7]=2)[CH2:40][C:39]1=[O:44]Komponenten
3
Edukt 2
Produkt 1
Versuchsvorschrift
Following the procedure of Example 224, tert-butyl (3S)-1-(6-(5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ylcarbamate and 1-methylpiperazin-2-one were reacted and deprotected by the procedure of Example 229. The mixture was purified by lyophilization from water and trituration of the crude product with cold methanol. The solid material was collected by filtration to afford 52 mg (28%) of 223 over two steps. ESI MS m/z 393.2 (M+1). 1H NMR (400 MHz, DMSO) δ 13.55 (s, 1H), 9.07 (s, 2H), 8.81 (s, 1H), 7.73 (t, J=8.0 Hz, 1H), 7.60 (s, 1H), 7.52 (d, J=7.5 Hz, 1H), 6.92 (d, J=8.5 Hz, 1H), 3.95 (s, 2H), 3.88 (m, 6H), 3.48-3.44 (m, 2H), 3.31 (s, 4H), 2.91 (s, 3H)