HCID 118131060, compound → HCID 118131393, compound

HRID 634500Notes

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][CH:17]=[C:16]([CH2:20][N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[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:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]5[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]5)[CH:15]=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

Reactant 2

HCID 118131060HCID 118131060, compound

HCID 178492931HCID 178492931, compound

Product 1

HCID 118131393HCID 118131393, compoundYield 34.2%

Procedure

The title compound was made in a similar way as that of example 134, step a, from 3-(1-hydroxyethyl)-4-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-isochromen-1-one (Intermediate B49, 350 mg, 0.925 mmol) and 3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate G1, 264 mg, 1.017 mmol) to give 3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-isochromen-1-one (196 mg, 0.316 mmol, 34.2% yield) as a brown solid.

Sources & evidence

ORD record: ord-9e97cac5382b44258e242b55cc083740
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321776B2

Reaction notes

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