(R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-one → (R)-3-[2-[[2-[4-(Benzyloxy)-3-(hydroxymethyl)phenyl]-2-hydroxyethyl]-amino]-2-methylpropyl]-N-[[1,6-diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]benzamide

HRID 385277Notes

Reaction equation

HRID 385277 reaction equation
N(C[C@@H](C1C=CC(OCC2C=CC=CC=2)=C2C=1C=CC(=O)N2)O)=[N+]=[N-].[CH2:26]([O:33][C:34]1[CH:39]=[CH:38][C:37]([C@@H:40]([O:77][Si](C(C)(C)C)(C)C)[CH2:41][NH:42][C:43]([CH3:76])([CH3:75])[CH2:44][C:45]2[CH:46]=[C:47]([CH:72]=[CH:73][CH:74]=2)[C:48]([NH:50][CH2:51][C:52]2[C:53]([NH:65][CH:66]3[CH2:71][CH2:70][O:69][CH2:68][CH2:67]3)=[C:54]3[CH:62]=[N:61][N:60]([CH2:63][CH3:64])[C:55]3=[N:56][C:57]=2[CH2:58][CH3:59])=[O:49])=[CH:36][C:35]=1[CH2:85][O:86][Si](C(C)(C)C)(C)C)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([O:33][C:34]1[CH:39]=[CH:38][C:37]([C@@H:40]([OH:77])[CH2:41][NH:42][C:43]([CH3:75])([CH3:76])[CH2:44][C:45]2[CH:46]=[C:47]([CH:72]=[CH:73][CH:74]=2)[C:48]([NH:50][CH2:51][C:52]2[C:53]([NH:65][CH:66]3[CH2:67][CH2:68][O:69][CH2:70][CH2:71]3)=[C:54]3[CH:62]=[N:61][N:60]([CH2:63][CH3:64])[C:55]3=[N:56][C:57]=2[CH2:58][CH3:59])=[O:49])=[CH:36][C:35]=1[CH2:85][OH:86])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 58505170(R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-oneHCID 86659066(R)-3-[2-[[2-[4-(Benzyloxy)-3-[[(tert-butyldimethylsilyl)oxy]methyl]phenyl]-2-[(tert-butyldimethylsilyl)oxy]ethyl]amino]-2-methylpropyl]-N-[[1,6-diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]benzamide

Product 1

HCID 66989983(R)-3-[2-[[2-[4-(Benzyloxy)-3-(hydroxymethyl)phenyl]-2-hydroxyethyl]-amino]-2-methylpropyl]-N-[[1,6-diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]benzamide

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 3, using Intermediate 51 as a substrate. ES/MS calcd. for C43H55N6O5+ 735.2. found m/z=735.5 (M+H)+.

Sources & evidence

ORD record
ord-606a18c28298461e8678ae2ebe4c2cf7
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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