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(R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-one → (R)-N-[[1,6-diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-[5-[[2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]pentyl]benzamide

HRID 385288
Notes
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Reaction equation

HRID 385288 reaction equation
N(C[C@@H](C1C=CC(OCC2C=CC=CC=2)=C2C=1C=CC(=O)N2)O)=[N+]=[N-].[Si]([O:33][C@H:34]([C:72]1[CH:81]=[CH:80][C:79]([OH:82])=[C:78]2[C:73]=1[CH:74]=[CH:75][C:76](=[O:83])[NH:77]2)[CH2:35][NH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]1[CH:71]=[CH:70][C:45]([C:46]([NH:48][CH2:49][C:50]2[C:51]([NH:63][CH:64]3[CH2:69][CH2:68][O:67][CH2:66][CH2:65]3)=[C:52]3[CH:60]=[N:59][N:58]([CH2:61][CH3:62])[C:53]3=[N:54][C:55]=2[CH2:56][CH3:57])=[O:47])=[CH:44][CH:43]=1)(C(C)(C)C)(C)C>>[CH2:61]([N:58]1[C:53]2=[N:54][C:55]([CH2:56][CH3:57])=[C:50]([CH2:49][NH:48][C:46](=[O:47])[C:45]3[CH:70]=[CH:71][C:42]([CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][NH:36][CH2:35][C@H:34]([OH:33])[C:72]4[CH:81]=[CH:80][C:79]([OH:82])=[C:78]5[C:73]=4[CH:74]=[CH:75][C:76](=[O:83])[NH:77]5)=[CH:43][CH:44]=3)[C:51]([NH:63][CH:64]3[CH2:69][CH2:68][O:67][CH2:66][CH2:65]3)=[C:52]2[CH:60]=[N:59]1)[CH3:62]
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 58505170(R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-oneHCID 66989901(R)-4-[5-[[2-[[tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]pentyl]-N-[[1,6-diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]benzamide

Product 1

HCID 53495161(R)-N-[[1,6-diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-[5-[[2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]pentyl]benzamide

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 3, using Intermediate 44 as substrate.

Sources & evidence

ORD record
ord-034fa12721ec431da9c98915b39a06f9
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367829B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes