3-(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 dihydrochloride → 3-(1-(4-amino-3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(4-(3-(dimethylamino)prop-1-en-1-yl)phenyl)-1H-isochromen-1-one

HRID 634495Notes

Reaction equation

HRID 634495 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.[CH3:46][N:47]([CH3:71])[CH2:48][CH:49]=[CH:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]2[C:66]3[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=3)[C:60](=[O:67])[O:59][C:58]=2[CH:68](O)[CH3:69])=[CH:53][CH:52]=1.[CH2:72]([O:79][C:80]1[CH:81]=[C:82]([C:87]2[C:95]3[C:90](=[N:91][CH:92]=[N:93][C:94]=3[NH2:96])[NH:89][N:88]=2)[CH:83]=[C:84]([F:86])[CH:85]=1)[C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1>>[NH2:96][C:94]1[N:93]=[CH:92][N:91]=[C:90]2[N:89]([CH:68]([C:58]3[O:59][C:60](=[O:67])[C:61]4[C:66]([C:57]=3[C:54]3[CH:53]=[CH:52][C:51]([CH:50]=[CH:49][CH2:48][N:47]([CH3:46])[CH3:71])=[CH:56][CH:55]=3)=[CH:65][CH:64]=[CH:63][CH:62]=4)[CH3:69])[N:88]=[C:87]([C:82]3[CH:83]=[C:84]([F:86])[CH:85]=[C:80]([O:79][CH2:72][C:73]4[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=4)[CH:81]=3)[C:95]=12

Participants

4

Reactant 3

HCID 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 1232862894-(4-(3-(dimethylamino)prop-1-en-1-yl)phenyl)-3-(1-hydroxyethyl)-1H-isochromen-1-one2×HCID 1785087223-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 1238704623-(1-(4-amino-3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(4-(3-(dimethylamino)prop-1-en-1-yl)phenyl)-1H-isochromen-1-oneYield 43.1%

Procedure

The title compound was made in a similar way as that of the compound of example 134, step a, from 4-(4-(3-(dimethylamino)prop-1-en-1-yl)phenyl)-3-(1-hydroxyethyl)-1H-isochromen-1-one (intermediate B45, 220 mg, 0.630 mmol) and 3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate G18, 0.63 mmol, 211 mg) to give 3-(1-(4-amino-3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(4-(3-(dimethylamino)prop-1-en-1-yl)phenyl)-1H-isochromen-1-one (120 mg, 0.18 mmol, 43.1% yield) as a yellow oil.

Sources & evidence

ORD record
ord-9e1ea651f8cb4698b014ed7daa590385
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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