3-(1-hydroxyethyl)-4-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-isochromen-1-one → 3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-isochromen-1-one

HRID 634491Notes

Reaction equation

HRID 634491 reaction equation
Cl.Cl.NC1N=CN=C2N(C(C3OC(=O)C4C(C=3C3SC(CN5CCNCC5)=CC=3)=CC=CC=4)C)N=C(C3C=C(O)C=C(F)C=3)C=12.O[CH:47]([C:49]1[O:50][C:51](=[O:72])[C:52]2[C:57]([C:58]=1[C:59]1[S:60][C:61]([CH2:64][N:65]3[CH2:70][CH2:69][N:68]([CH3:71])[CH2:67][CH2:66]3)=[CH:62][CH:63]=1)=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH3:48].[F:73][C:74]1[CH:75]=[C:76]([C:82]2[C:90]3[C:85](=[N:86][CH:87]=[N:88][C:89]=3[NH2:91])[NH:84][N:83]=2)[CH:77]=[C:78]([O:80][CH3:81])[CH:79]=1>>[NH2:91][C:89]1[N:88]=[CH:87][N:86]=[C:85]2[N:84]([CH:47]([C:49]3[O:50][C:51](=[O:72])[C:52]4[C:57]([C:58]=3[C:59]3[S:60][C:61]([CH2:64][N:65]5[CH2:70][CH2:69][N:68]([CH3:71])[CH2:67][CH2:66]5)=[CH:62][CH:63]=3)=[CH:56][CH:55]=[CH:54][CH:53]=4)[CH3:48])[N:83]=[C:82]([C:76]3[CH:77]=[C:78]([O:80][CH3:81])[CH:79]=[C:74]([F:73])[CH:75]=3)[C:90]=12

Participants

4

Reactant 3

HCID 1181313643-(1-hydroxyethyl)-4-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-isochromen-1-oneHCID 1181314923-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(5-(piperazin-1-ylmethyl)thiophen-2-yl)-1H-isochromen-1-one dihydrochlorideHCID 178492931HCID 178492931, compound

Product 1

HCID 1181315073-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-isochromen-1-oneYield 62.8%

Procedure

The title compound was made in a similar way as that of the compound of example 134, step a, from 3-(1-hydroxyethyl)-4-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-isochromen-1-one (Intermediate B39, 411 mg, 1.069 mmol), and 3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (intermediate G1, 305 mg, 1.176 mmol) to give 3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-isochromen-1-one (420 mg, 0.671 mmol, 62.8% yield) as a brown solid.

Sources & evidence

ORD record
ord-c9fcae36fec14c7ebceef62fc4e8d688
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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