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-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 634493Notes

Reaction equation

HRID 634493 reaction equation
Cl.Cl.NC1N=CN=C2N([CH:21]([C:23]3[O:24][C:25](=[O:45])[C:26]4[C:31]([C:32]=3[C:33]3[S:34][C:35]([CH2:38][N:39]5[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]5)=[CH:36][CH:37]=3)=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH3:22])N=C(C3C=C(O)C=C(F)C=3)C=12.[CH3:46]N(C)CC=CC1C=C(C2C3C(=CC=CC=3)C(=O)OC=2C(O)C)C=CC=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)C1C=CC=CC=1>>[NH2:96][C:94]1[N:93]=[CH:92][N:91]=[C:90]2[N:89]([CH:21]([C:23]3[O:24][C:25](=[O:45])[C:26]4[C:31]([C:32]=3[C:33]3[S:34][C:35]([CH2:38][N:39]5[CH2:40][CH2:41][N:42]([CH3:46])[CH2:43][CH2:44]5)=[CH:36][CH:37]=3)=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH3:22])[N:88]=[C:87]([C:82]3[CH:81]=[C:80]([O:79][CH3:72])[CH:85]=[C:84]([F:86])[CH:83]=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 1237222694-(3-(3-(dimethylamino)prop-1-en-1-yl)phenyl)-3-(1-hydroxyethyl)-1H-isochromen-1-oneHCID 1785087223-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

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 43%

Procedure

The title compound was made in a similar way as that of the compound of example 134, step a, from 4-(3-(3-(dimethylamino)prop-1-en-1-yl)phenyl)-3-(1-hydroxyethyl)-1H-isochromen-1-one (Intermediate B42, 280 mg, 0.801 mmol), and 3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate G-18, 0.417 mmol, 140 mg) 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 (120 mg, 0.18 mmol, 43% yield) as a yellow oil.

Sources & evidence

ORD record
ord-68e61aa37a8346ca8affdd818be4a42c
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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