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

HRID 1775035Notes

Reaction equation

HRID 1775035 reaction equation
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]

Participants

3

Reactant 2

HCID 43990421-Methylpiperazin-2-oneHCID 86676698HCID 86676698, compound

Product 1

HCID 712539601-methyl-4-{3-[6-(piperazin-1-yl)pyridin-2-yl]-1H-pyrazolo[3,4-c]pyridin-5-yl}piperazin-2-oneYield 28%

Procedure

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)

Workup

  1. customwere reacted
  2. customThe mixture was purified by lyophilization from water and trituration of the crude product with cold methanol
  3. filtrationThe solid material was collected by filtration

Sources & evidence

ORD record
ord-6a6678b5916e4f38b7286abdca8bcc82
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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