1-Methylpiperazine → N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 550470Notes

Reaction equation

HRID 550470 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.[CH3:31][N: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][N:32]([CH3:31])[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 531671-MethylpiperazineHCID 117050313-(2-chloroethoxy)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 11649197N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 16%

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 (prepared as described in Example 12) and N-methylpiperazine to give the title compound in 16% yield; NMR Spectrum: 2.10 (s, 3H), 2.28 (br s, 4H), 2.50 (hidden by DMSO, 4H), 2.77 (t, 2H), 4.41 (t, 2H), 5.25 (s, 2H), 7.19 (t, 1H), 7.23 (d, 1H), 7.29-7.33 (m, 2H), 7.44-7.48 (m, 1H), 7.57 (d, 1H), 7.89-7.91 (m, 1H), 8.29 (s, 1H), 8.53 (br s, 1H); Mass Spectrum: 512 (MH+).

Sources & evidence

ORD record
ord-3104427e0bf0453c9f578b8ff95c961c
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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