(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]-3-[[[2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]methyl]benzamide

HRID 385286Notes

Reaction equation

HRID 385286 reaction equation
N(C[C@@H](C1C=CC(OCC2C=CC=CC=2)=C2C=1C=CC(=O)N2)O)=[N+]=[N-].[Si]([O:33][CH2:34][C:35]1[CH:36]=[C:37]([C@@H:42]([OH:76])[CH2:43][NH:44][CH2:45][C:46]2[CH:47]=[C:48]([CH:73]=[CH:74][CH:75]=2)[C:49]([NH:51][CH2:52][C:53]2[C:54]([NH:66][CH:67]3[CH2:72][CH2:71][O:70][CH2:69][CH2:68]3)=[C:55]3[CH:63]=[N:62][N:61]([CH2:64][CH3:65])[C:56]3=[N:57][C:58]=2[CH2:59][CH3:60])=[O:50])[CH:38]=[CH:39][C:40]=1[OH:41])(C(C)(C)C)(C)C>N1C=CC=CC=1>[CH2:64]([N:61]1[C:56]2=[N:57][C:58]([CH2:59][CH3:60])=[C:53]([CH2:52][NH:51][C:49](=[O:50])[C:48]3[CH:73]=[CH:74][CH:75]=[C:46]([CH2:45][NH:44][CH2:43][C@H:42]([OH:76])[C:37]4[CH:38]=[CH:39][C:40]([OH:41])=[C:35]([CH2:34][OH:33])[CH:36]=4)[CH:47]=3)[C:54]([NH:66][CH:67]3[CH2:68][CH2:69][O:70][CH2:71][CH2:72]3)=[C:55]2[CH:63]=[N:62]1)[CH3:65]

Participants

4

Reactant 2

HCID 58505170(R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-oneHCID 58505276(R)-3-[[[2-(3-[[(tert-Butyldimethylsilyl)oxy]methyl]-4-hydroxyphenyl]-2-hydroxyethyl]amino]methyl]-N-[[1,6-diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]benzamide

Product 1

HCID 54588809(R)-N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-3-[[[2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]methyl]benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 3, using HF pyridine in place of TBAF and Intermediate 45 as a substrate.

Sources & evidence

ORD record
ord-5e09422cc6d44b44ad0e5dd8fd4a1ca3
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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