(R)-5-(2-Amino-1-hydroxyethyl)-8-hydroxyquinolin-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-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl]ethyl]amino]methyl]benzamide

HRID 385285Notes

Reaction equation

HRID 385285 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:16])[NH:10]2)[OH:4].[CH2:17]([N:19]1[C:23]2=[N:24][C:25]([CH2:47][CH3:48])=[C:26]([CH2:35][NH:36][C:37](=[O:46])[C:38]3[CH:43]=[CH:42][C:41]([CH:44]=O)=[CH:40][CH:39]=3)[C:27]([NH:28][CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[C:22]2[CH:21]=[N:20]1)[CH3:18]>>[CH2:17]([N:19]1[C:23]2=[N:24][C:25]([CH2:47][CH3:48])=[C:26]([CH2:35][NH:36][C:37](=[O:46])[C:38]3[CH:39]=[CH:40][C:41]([CH2:44][NH:1][CH2:2][C@H:3]([OH:4])[C:5]4[CH:14]=[CH:13][C:12]([OH:15])=[C:11]5[C:6]=4[CH:7]=[CH:8][C:9](=[O:16])[NH:10]5)=[CH:42][CH:43]=3)[C:27]([NH:28][CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[C:22]2[CH:21]=[N:20]1)[CH3:18]

Participants

3

Reactant 2

HCID 24996153(R)-5-(2-Amino-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-oneHCID 58505284N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-formylbenzamide

Product 1

HCID 54588808(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-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl]ethyl]amino]methyl]benzamide

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 43, using Intermediate 4 in place of Intermediate 8 and Intermediate 31 in place of Intermediate 29.

Sources & evidence

ORD record
ord-1f9c991855354748b2d86383b35675e8
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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