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-(5-(3-(dimethylamino)prop-1-en-1-yl)thiophen-2-yl)-1H-isochromen-1-one

HRID 634492Notes

Reaction equation

HRID 634492 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]([CH3:70])[CH2:48][CH:49]=[CH:50][C:51]1[S:55][C:54]([C:56]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[C:59](=[O:66])[O:58][C:57]=2[CH:67](O)[CH3:68])=[CH:53][CH:52]=1.[CH2:71]([O:78][C:79]1[CH:80]=[C:81]([C:86]2[C:94]3[C:89](=[N:90][CH:91]=[N:92][C:93]=3[NH2:95])[NH:88][N:87]=2)[CH:82]=[C:83]([F:85])[CH:84]=1)[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1>>[NH2:95][C:93]1[N:92]=[CH:91][N:90]=[C:89]2[N:88]([CH:67]([C:57]3[O:58][C:59](=[O:66])[C:60]4[C:65]([C:56]=3[C:54]3[S:55][C:51]([CH:50]=[CH:49][CH2:48][N:47]([CH3:70])[CH3:46])=[CH:52][CH:53]=3)=[CH:64][CH:63]=[CH:62][CH:61]=4)[CH3:68])[N:87]=[C:86]([C:81]3[CH:82]=[C:83]([F:85])[CH:84]=[C:79]([O:78][CH2:71][C:72]4[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=4)[CH:80]=3)[C:94]=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 1237356434-(5-(3-(dimethylamino)prop-1-en-1-yl)thiophen-2-yl)-3-(1-hydroxyethyl)-1H-isochromen-1-oneHCID 1785087223-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 1232548383-(1-(4-amino-3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(5-(3-(dimethylamino)prop-1-en-1-yl)thiophen-2-yl)-1H-isochromen-1-oneYield 72,432.398%

Procedure

The title compound was made in a similar way as that of the compound of example 134, step a, from 4-(5-(3-(dimethylamino)prop-1-en-1-yl)thiophen-2-yl)-3-(1-hydroxyethyl)-1H-isochromen-1-one (Intermediate B40, 220 mg, 0,619 mmol), and 3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate G18, 125 mg, 0.37 mmol) to give 3-(1-(4-amino-3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(5-(3-(dimethylamino)prop-1-en-1-yl)thiophen-2-yl)-1H-isochromen-1-one (180 mg, 0,268 mmol, 43.2% yield) as a brown oil.

Sources & evidence

ORD record
ord-138b9815ae1c4a17bbb3082652123b1b
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

Loading…