N-(3-(6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide → N-(3-(6-((3-fluoro-5-hydroxy-4-morpholinophenyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide

HRID 929684Notes

Reaction equation

HRID 929684 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[N:9]=[CH:10][C:5]2=[C:4]([C:17]2[CH:18]=[C:19]([NH:23][C:24](=[O:27])[CH:25]=[CH2:26])[CH:20]=[CH:21][CH:22]=2)[N:3]=1.[NH2:28][C:29]1[CH:30]=[C:31]([F:42])[C:32]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[C:33]([OH:35])[CH:34]=1>>[F:42][C:31]1[CH:30]=[C:29]([NH:28][C:2]2[N:7]=[C:6]3[N:8]([CH:11]4[CH2:16][CH2:15][CH2:14][CH2:13][O:12]4)[N:9]=[CH:10][C:5]3=[C:4]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:27])[CH:25]=[CH2:26])[CH:20]=[CH:21][CH:22]=3)[N:3]=2)[CH:34]=[C:33]([OH:35])[C:32]=1[N:36]1[CH2:37][CH2:38][O:39][CH2:40][CH2:41]1

Participants

3

Reactant 2

HCID 86677518N-(3-(6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamideHCID 900945885-Amino-3-fluoro-2-morpholinophenol

Product 1

HCID 90095134N-(3-(6-((3-fluoro-5-hydroxy-4-morpholinophenyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide

Procedure

N-(3-(6-Chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide can then be reacted with 5-amino-3-fluoro-2-morpholinophenol under palladium catalyzed aminolysis conditions to yield N-(3-(6-((3-fluoro-5-hydroxy-4-morpholinophenyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide, which can be deprotected under mild acidic conditions to provide N-(3-(6-((3-fluoro-5-hydroxy-4-morpholinophenyl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide.

Sources & evidence

ORD record
ord-78fe517f2d334593b4f028afd1c698cf
Source dataset
uspto-grants-2016_03
Patent number
US09296703B2

Reaction notes

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