(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one → HCID 59145945, compound

HRID 2383376Notes

Reaction equation

HRID 2383376 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][N:19]3[CH:23]=[N:22][C:21]([C:24]([CH:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[OH:25])=[N:20]3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1.[CH2:38]([O:45][C:46]1[CH:47]=[CH:48][C:49]([C@@H:57]([O:60][Si:61]([C:64]([CH3:67])([CH3:66])[CH3:65])([CH3:63])[CH3:62])[CH2:58]Br)=[C:50]2[C:55]=1[NH:54][C:53](=[O:56])[CH:52]=[CH:51]2)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[CH2:38]([O:45][C:46]1[CH:47]=[CH:48][C:49]([C@@H:57]([O:60][Si:61]([C:64]([CH3:65])([CH3:67])[CH3:66])([CH3:63])[CH3:62])[CH2:58][NH:1][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][CH:15]([CH2:18][N:19]4[CH:23]=[N:22][C:21]([C@:24]([CH:32]5[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]5)([OH:25])[C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)=[N:20]4)[CH2:16][CH2:17]3)=[CH:8][CH:9]=2)=[C:50]2[C:55]=1[NH:54][C:53](=[O:56])[CH:52]=[CH:51]2)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

3

Reactant 2

HCID 15606253(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-oneHCID 67029376HCID 67029376, compound

Product 1

HCID 59145945HCID 59145945, compoundYield 40%

Procedure

The title compound was prepared from (R)-({-[(1-{2-[4-(2-aminoethyl)phenyl]ethyl}piperidin-4-yl)methyl]-1H-1,2,4-triazol-3-yl}(cyclohexyl)phenylmethanol (Preparation 13, 2.57 g, 5.12 mmol) and 8-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]quinolin-2(1H)-one (WO2005/09286, 2.50 g, 5.12 mmol) using the same method as described in preparation 7 to give a white solid, in 40% yield, 2.3 g.

Workup

  1. customas described in preparation 7
  2. customto give a white solid

Sources & evidence

ORD record
ord-481246fc972c45c58923e992c78d61e5
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

Loading…