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

HRID 385287Notes

Reaction equation

HRID 385287 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:75]=[CH:74][C:49]([C:50]([NH:52][CH2:53][C:54]3[C:55]([NH:67][CH:68]4[CH2:73][CH2:72][O:71][CH2:70][CH2:69]4)=[C:56]4[CH:64]=[N:63][N:62]([CH2:65][CH3:66])[C:57]4=[N:58][C:59]=3[CH2:60][CH3:61])=[O:51])=[CH:48][CH:47]=2)[CH:38]=[CH:39][C:40]=1[OH:41])(C(C)(C)C)(C)C>N1C=CC=CC=1>[CH2:65]([N:62]1[C:57]2=[N:58][C:59]([CH2:60][CH3:61])=[C:54]([CH2:53][NH:52][C:50](=[O:51])[C:49]3[CH:48]=[CH:47][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:75][CH:74]=3)[C:55]([NH:67][CH:68]3[CH2:69][CH2:70][O:71][CH2:72][CH2:73]3)=[C:56]2[CH:64]=[N:63]1)[CH3:66]

Participants

4

Reactant 2

HCID 58505170(R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-oneHCID 66990074(R)-4-[[[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 54588810(R)-N-[[1,6-diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-[[[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 46 as a substrate.

Sources & evidence

ORD record
ord-f602ccfa95df44ae99bbf6dd1ca5a0ed
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

Loading…