(R)-N-(4-(5-((2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)pent-1-yn-1-yl)phenyl)-2,2,2-trifluoroacetamide → (R)-1-(4-(5-((2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)pent-1-yn-1-yl)phenyl)-3-((1,6-diethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)urea

HRID 385280Notes

Reaction equation

HRID 385280 reaction equation
[Si:1]([O:8][C@H:9]([C:30]1[CH:39]=[CH:38][C:37]([OH:40])=[C:36]2[C:31]=1[CH:32]=[CH:33][C:34](=[O:41])[NH:35]2)[CH2:10][NH:11]CCCC#CC1C=CC(NC(=O)C(F)(F)F)=CC=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[CH2:43][CH2:44][CH2:45][C:46]#[C:47][C:48]1[CH:53]=[CH:52][C:51]([NH:54][C:55]([NH:57][CH2:58][C:59]2[C:60]([NH:72][CH:73]3[CH2:78][CH2:77][O:76][CH2:75][CH2:74]3)=[C:61]3[CH:69]=[N:68][N:67]([CH2:70][CH3:71])[C:62]3=[N:63][C:64]=2[CH2:65][CH3:66])=[O:56])=[CH:50][CH:49]=1>>[Si:1]([O:8][C@H:9]([C:30]1[CH:39]=[CH:38][C:37]([OH:40])=[C:36]2[C:31]=1[CH:32]=[CH:33][C:34](=[O:41])[NH:35]2)[CH2:10][NH:11][CH2:43][CH2:44][CH2:45][C:46]#[C:47][C:48]1[CH:53]=[CH:52][C:51]([NH:54][C:55]([NH:57][CH2:58][C:59]2[C:60]([NH:72][CH:73]3[CH2:74][CH2:75][O:76][CH2:77][CH2:78]3)=[C:61]3[CH:69]=[N:68][N:67]([CH2:70][CH3:71])[C:62]3=[N:63][C:64]=2[CH2:65][CH3:66])=[O:56])=[CH:50][CH:49]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 58505275(R)-N-(4-(5-((2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)pent-1-yn-1-yl)phenyl)-2,2,2-trifluoroacetamideHCID 585052951-(4-(5-bromopent-1-yn-1-yl)phenyl)-3-((1,6-diethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)urea

Product 1

HCID 58505291(R)-1-(4-(5-((2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)pent-1-yn-1-yl)phenyl)-3-((1,6-diethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)urea

Procedure

The title compound was prepared in a manner analogous to that described for Intermediate 37, using Intermediate 35 in place of Intermediate 26. ES/MS calcd. for C45H61N8O5Si+ 821.5. found m/z=821.6 (M+H)+.

Sources & evidence

ORD record
ord-345e4582e21f463dbdb503e8dcef68b2
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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