Piperidin-4-ol → 1-{2-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}piperidin-4-ol

HRID 550484Notes

Reaction equation

HRID 550484 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.[OH:35][CH: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][CH:36]([OH: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 79341Piperidin-4-olHCID 115114392-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl methanesulfonate

Product 1

HCID 115694341-{2-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}piperidin-4-olYield 54%

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 4-hydroxypiperidine to give the title compound in 54% yield; NMR Spectrum: 1.36 (d, 2H), 1.69 (d, 2H), 2.18 (t, 2H), 2.78 (m, 4H), 3.81 (s, 3H), 4.41 (t, 2H), 4.53 (d, 1H), 5.16 (s, 2H), 7.03 (d, 1H), 7.23 (dd, 1H), 7.37 (m, 2H), 7.54 (d, 1H), 7.85 (td, 1H), 8.26 (s, 1H), 8.30 (s, 1H), 8.58 (d, 1H); Mass Spectrum: 492 (MH+).

Sources & evidence

ORD record
ord-fa5363d3316e43c5adb64048150b2074
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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