3-(1-hydroxyethyl)-4-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-isochromen-1-one → 3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-isochromen-1-one

HRID 634497Notes

Reaction equation

HRID 634497 reaction equation
O[CH:2]([C:4]1[O:5][C:6](=[O:28])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)=[CH:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3].[F:29][C:30]1[CH:31]=[C:32]([C:38]2[C:46]3[C:41](=[N:42][CH:43]=[N:44][C:45]=3[NH2:47])[NH:40][N:39]=2)[CH:33]=[C:34]([O:36][CH3:37])[CH:35]=1>>[NH2:47][C:45]1[N:44]=[CH:43][N:42]=[C:41]2[N:40]([CH:2]([C:4]3[O:5][C:6](=[O:28])[C:7]4[C:12]([C:13]=3[C:14]3[CH:15]=[CH:16][C:17]([CH2:20][N:21]5[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]5)=[CH:18][CH:19]=3)=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH3:3])[N:39]=[C:38]([C:32]3[CH:33]=[C:34]([O:36][CH3:37])[CH:35]=[C:30]([F:29])[CH:31]=3)[C:46]=12

Participants

3

Reactant 2

HCID 1181314553-(1-hydroxyethyl)-4-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-isochromen-1-oneHCID 178492931HCID 178492931, compound

Product 1

HCID 1181313833-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-isochromen-1-oneYield 8%

Procedure

The title compound was made in a similar way as that of example 134, step a, from 3-(1-hydroxyethyl)-4-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-isochromen-1-one (Intermediate B46, 750 mg, 1.982 mmol) and 3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate G1, 565 mg, 2.18 mmol) to give 3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-isochromen-1-one (98 mg, 0.158 mmol, 7.98% yield) as a brown solid.

Sources & evidence

ORD record
ord-849cf8274f3a40cfab4edd0fe2505534
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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