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

HRID 550458Notes

Reaction equation

HRID 550458 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.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]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:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]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 8083MorpholineHCID 116548903-(2-chloroethoxy)-N-{3-chloro-4-[(6-methylpyridin-3-yl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 11540277N-{3-chloro-4-[(6-methylpyridin-3-yl)oxy]phenyl}-3-(2-morpholin-4-ylethoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 17%

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 (prepared as described in Example 16) and morpholine to give the title compound in 17% yield; NMR Spectrum: 2.45 (s, 3H), 2.50 (hidden by DMSO, 4H), 2.82 (t, 2H), 3.55-3.56 (m, 4H), 4.46 (t, 2H), 7.20 (d, 1H), 7.27 (s, 2H), 7.71 (d, 1H), 8.12 (s, 1H), 8.20 (s, 1H), 8.35 (s, 1H), 8.60 (br s, 1H); Mass Spectrum: 482 (MH+).

Sources & evidence

ORD record
ord-cf380a4dc1144064954321b821dda00d
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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