1-Methylpiperazine → N-[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 550483Notes

Reaction equation

HRID 550483 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[N:15][C:16]=2[NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[C:21]([O:33][CH3:34])[CH:20]=2)[NH:11][N:10]=1)(=O)=O.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>>[CH3:34][O:33][C:21]1[CH:20]=[C:19]([NH:18][C:16]2[N:15]=[CH:14][N:13]=[C:12]3[NH:11][N:10]=[C:9]([O:8][CH2:7][CH2:6][N:39]4[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]4)[C:17]=23)[CH:24]=[CH:23][C:22]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 115114392-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl methanesulfonate

Product 1

HCID 11656116N-[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 59%

Procedure

The procedure described in Example 55 was repeated using 2-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl methanesulfonate and N-methylpiperazine to give the title compound in 59% yield; NMR Spectrum: 2.10 (s, 3H), 2.52 (hidden by DMSO, 8H), 2.78 (t, 2H), 3.81 (s, 3H), 4.42 (t, 2H), 5.16 (s, 2H), 7.01 (d, 1H), 7.20 (dd, 1H), 7.36 (t+d, 2H), 7.54 (d, 1H), 7.84 (td, 1H), 8.26 (s, 1H), 8.36 (s, 1H), 8.58 (d, 1H); Mass Spectrum: 491 (MH+).

Sources & evidence

ORD record
ord-bfce0714e5674933904f0e729e531f90
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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