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

HRID 550471Notes

Reaction equation

HRID 550471 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]=[C:25]([F:29])[CH:24]=3)=[C:17]([Cl:30])[CH:16]=2)[NH:7][N:6]=1.[OH:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[Cl:30][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:35]4[CH2:36][CH2:37][CH:32]([OH:31])[CH2:33][CH2:34]4)[C:13]=23)[CH:20]=[CH:19][C:18]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1

Participants

3

Reactant 2

HCID 79341Piperidin-4-olHCID 117050313-(2-chloroethoxy)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 116204871-(2-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy}ethyl)piperidin-4-olYield 39%

Procedure

The procedure described in Example 23 was repeated using 3-(2-chloroethoxy)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine and 4-hydroxypiperidine to give the title compound in 39% yield; NMR Spectrum: 1.32-1.39 (m, 2H), 1.66-1.69 (m, 2H), 2.15 (t, 2H), 2.75-2.80 (m, 4H), 3.40-3.44 (m, 1H), 4.40 (t, 2H), 4.53 (br s, 1H), 5.25 (s, 2H), 7.18 (t, 1H), 7.23 (d, 1H), 7.29-7.33 (m, 2H), 7.44-7.47 (m, 1H), 7.56 (d, 1H), 7.90 (s, 1H), 8.29 (s, 1H), 8.50 (br s, 1H); Mass Spectrum: 513 (MH+).

Sources & evidence

ORD record
ord-6dd2a74a169148178132bbe864848c52
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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