(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one → 8-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({9-[4-((3-[cyclohexyl(hydroxy)phenyl methyl]-1H-1,2,4-triazol-1-yl}methyl)piperidin-1-yl]nonyl}-amino)ethyl]quinolin-2(1H)-one

HRID 2383381Notes

Reaction equation

HRID 2383381 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][N:18]2[CH:22]=[N:21][C:20]([C:23]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[OH:24])=[N:19]2)[CH2:13][CH2:12]1.[CH2:37]([O:44][C:45]1[CH:46]=[CH:47][C:48]([C@@H:56]([O:59][Si:60]([C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:62])[CH3:61])[CH2:57]Br)=[C:49]2[C:54]=1[NH:53][C:52](=[O:55])[CH:51]=[CH:50]2)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[CH2:37]([O:44][C:45]1[CH:46]=[CH:47][C:48]([C@@H:56]([O:59][Si:60]([C:63]([CH3:64])([CH3:66])[CH3:65])([CH3:62])[CH3:61])[CH2:57][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([CH2:17][N:18]3[CH:22]=[N:21][C:20]([C:23]([CH:31]4[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]4)([OH:24])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:19]3)[CH2:15][CH2:16]2)=[C:49]2[C:54]=1[NH:53][C:52](=[O:55])[CH:51]=[CH:50]2)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

3

Reactant 2

HCID 15606253(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-oneHCID 59145971(1-{[1-(9-aminononyl)piperidin-4-yl]methyl}-1H-1,2,4-triazol-3-yl)(cyclohexyl)phenylmethanol

Product 1

HCID 591459408-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({9-[4-((3-[cyclohexyl(hydroxy)phenyl methyl]-1H-1,2,4-triazol-1-yl}methyl)piperidin-1-yl]nonyl}-amino)ethyl]quinolin-2(1H)-oneYield 24%

Procedure

The title compound was prepared from (1-{[1-(9-aminononyl)piperidin-4-yl]methyl}-1H-1,2,4-triazol-3-yl)(cyclohexyl)phenylmethanol (Preparation 22, 150 mg, 0.303 mg) and 8-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]quinolin-2(1H)-one (WO05/09286, 148 mg, 0.303 mmol) using the same method as described in preparation 7, to give a clear oil, in 24% yield, 66 mg.

Workup

  1. customas described in preparation 7
  2. customto give a clear oil

Sources & evidence

ORD record
ord-b1c93129bd944edda10d25be915efc9c
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

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