Acryloyl chloride → HCID 68388399, compound

HRID 1500787Notes

Reaction equation

HRID 1500787 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[N:20]=[C:19]4[NH:21][N:22]=[CH:23][C:18]4=[C:17]([C:24]4[CH:25]=[C:26]([NH:30][C:31](=[O:34])[CH:32]=[CH2:33])[CH:27]=[CH:28][CH:29]=4)[N:16]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.NC1C=C(C2N=C(NC3C=CC(N4CCN(C)CC4)=CC=3)N=C3N([CH:65]4[CH2:70][CH2:69][CH2:68][CH2:67][O:66]4)N=CC=23)C=CC=1.C(Cl)(=O)C=C>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]3[N:20]=[C:19]4[N:21]([CH:65]5[CH2:70][CH2:69][CH2:68][CH2:67][O:66]5)[N:22]=[CH:23][C:18]4=[C:17]([C:24]4[CH:25]=[C:26]([NH:30][C:31](=[O:34])[CH:32]=[CH2:33])[CH:27]=[CH:28][CH:29]=4)[N:16]=3)=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 13140Acryloyl chlorideHCID 68388374HCID 68388374, compoundHCID 68388482HCID 68388482, compound

Product 1

HCID 68388399HCID 68388399, compound

Procedure

As an example, N-(3-(6-((4-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide be prepared according to Route III. Beginning with 4-(3-aminophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine, acylation with acryloyl chloride provides N-(3-(6-((4-(4-methylpiperazin-1-yl)phenyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide. Deprotection under mild acidic conditions yields N-(3-(6-((4-(4-methylpiperazin-1-yl)phenyl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide.

Sources & evidence

ORD record
ord-482758995dc84d6da691e9169ad64bb5
Source dataset
uspto-grants-2015_12
Patent number
US09206176B2

Reaction notes

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