1-Methylpiperazine → N-{3-chloro-4-[(6-methylpyridin-3-yl)oxy]phenyl}-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 550460Notes

Reaction equation

HRID 550460 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][C:22]3[CH:23]=[N:24][C:25]([CH3:28])=[CH:26][CH:27]=3)=[C:17]([Cl:29])[CH:16]=2)[NH:7][N:6]=1.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>>[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:34]4[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]4)[C:13]=23)[CH:20]=[CH:19][C:18]=1[O:21][C:22]1[CH:23]=[N:24][C:25]([CH3:28])=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 116548903-(2-chloroethoxy)-N-{3-chloro-4-[(6-methylpyridin-3-yl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 67020561N-{3-chloro-4-[(6-methylpyridin-3-yl)oxy]phenyl}-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 42%

Procedure

The procedure described in Example 23 was repeated using 3-(2-chloroethoxy)-N-{3-chloro-4-[(6-methylpyridin-3-yl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine and N-methylpiperazine to give the title compound in 42% yield; NMR Spectrum: 2.11 (s, 3H), 2.28 (br s, 4H), 2.45 (s, 3H), 2.50 (hidden by DMSO, 4H), 2.80 (t, 2H), 4.44 (t, 2H), 7.20 (d, 1H), 7.26 (br s, 2H), 7.72 (d, 1H), 8.11 (s, 1H), 8.20 (s, 1H), 8.36 (s, 1H), 8.59 (br s, 1H); Mass Spectrum: 495 (MH+).

Sources & evidence

ORD record
ord-66fd1960260c474fb5af56b740207ae0
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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