3-(1-(4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one → N-(5-(4-amino-1-(1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

HRID 634475Notes

Reaction equation

HRID 634475 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:17]([C:19]3[O:20][C:21](=[O:35])[C:22]4[C:27]([C:28]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH3:18])[N:9]=[C:10](C3C=NC=CN=3)[C:3]=12.[F:36][C:37]1[CH:42]=[CH:41][C:40]([S:43]([NH:46][C:47]2[CH:48]=[N:49][CH:50]=[C:51]([Sn](C)(C)C)[CH:52]=2)(=[O:45])=[O:44])=[CH:39][CH:38]=1.NC1N=CN=C2N(C(C3OC(=O)C4C(C=3C3C=CC=CC=3)=CC=CC=4)C)N=C(I)C=12>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:17]([C:19]3[O:20][C:21](=[O:35])[C:22]4[C:27]([C:28]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH3:18])[N:9]=[C:10]([C:51]3[CH:52]=[C:47]([NH:46][S:43]([C:40]4[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=4)(=[O:45])=[O:44])[CH:48]=[N:49][CH:50]=3)[C:3]=12

Participants

4

Reactant 3

HCID 1181310533-(1-(4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-oneHCID 1181312833-(1-(4-amino-3-(pyrazin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-oneHCID 1317354824-fluoro-N-(5-(trimethylstannyl)pyridin-3-yl)benzenesulfonamide

Product 1

HCID 118131380N-(5-(4-amino-1-(1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)pyridin-3-yl)-4-fluorobenzenesulfonamideYield 17.4%

Procedure

The title compound was made in a similar way as that of the compound of example 52 from 4-fluoro-N-(5-(trimethylstannyl)pyridin-3-yl)benzenesulfonamide (Intermediate G9, 98 mg, 0.236 mmol) and 3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one (intermediate D2a, 60 mg, 0.118 mmol) affording the title compound (13 mg, 0.021 mmol, 17.4% yield) as white solid

Sources & evidence

ORD record
ord-f016e8f7292c46e3be2c02480e14d120
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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