Piperazin-2-one → 4-{2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}piperazin-2-one

HRID 550433Notes

Reaction equation

HRID 550433 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[N:11][C:12]=2[NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[C:17]([Cl:29])[CH:16]=2)[NH:7][N:6]=1.[NH:30]1[CH2:35][CH2:34][NH:33][CH2:32][C:31]1=[O:36]>>[Cl:29][C:17]1[CH:16]=[C:15]([NH:14][C:12]2[N:11]=[CH:10][N:9]=[C:8]3[NH:7][N:6]=[C:5]([O:4][CH2:3][CH2:2][N:33]4[CH2:34][CH2:35][NH:30][C:31](=[O:36])[CH2:32]4)[C:13]=23)[CH:20]=[CH:19][C:18]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

3

Reactant 2

HCID 231360Piperazin-2-oneHCID 115028913-(2-chloroethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 115477634-{2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}piperazin-2-oneYield 28%

Procedure

The procedure described in Example 23 was repeated using 3-(2-chloroethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine and piperazinone to give the title compound in 28% yield; NMR Spectrum: 2.70 (t, 2H), 2.89 (t, 2H), 3.09 (s, 2H), 3.14-3.17 (m, 2H), 4.45 (t, 2H), 5.29 (s, 2H), 7.23 (d, 1H), 7.37 (t, 1H), 7.55-7.58 (m, 2H), 7.73 (br s, 1H), 7.87 (t, 1H), 7.92 (s, 1H), 8.29 (s, 1H), 8.48 (br s, 1H), 8.59 (s, 1H); Mass Spectrum: 495 (MH+).

Sources & evidence

ORD record
ord-669bb15f1fcc4aee92e53a15f4b0b275
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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