(2S)-1-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-3-({4-[2-(2-cyclopentylethyl)-3H-imidazo[4,5-b]pyridin-3-yl]phenethyl}amino)-2-propanol → 4-[(2S)-3-(2-{4-[2-(2-Cyclopentyl-ethyl)-imidazo[4,5-b]pyridin-3-yl]-phenyl}-ethylamino)-2-hydroxy-propoxy]-phenol

HRID 1862778Notes

Reaction equation

HRID 1862778 reaction equation
[Si]([O:18][C:19]1[CH:54]=[CH:53][C:22]([O:23][CH2:24][C@@H:25]([OH:52])[CH2:26][NH:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([N:36]3[C:40]4=[N:41][CH:42]=[CH:43][CH:44]=[C:39]4[N:38]=[C:37]3[CH2:45][CH2:46][CH:47]3[CH2:51][CH2:50][CH2:49][CH2:48]3)=[CH:32][CH:31]=2)=[CH:21][CH:20]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)(Cl)Cl.CO>[CH:47]1([CH2:46][CH2:45][C:37]2[N:36]([C:33]3[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][NH:27][CH2:26][C@H:25]([OH:52])[CH2:24][O:23][C:22]4[CH:53]=[CH:54][C:19]([OH:18])=[CH:20][CH:21]=4)=[CH:31][CH:32]=3)[C:40]3=[N:41][CH:42]=[CH:43][CH:44]=[C:39]3[N:38]=2)[CH2:48][CH2:49][CH2:50][CH2:51]1

Participants

3

Reactant 1

HCID 70008209(2S)-1-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-3-({4-[2-(2-cyclopentylethyl)-3H-imidazo[4,5-b]pyridin-3-yl]phenethyl}amino)-2-propanol

Product 1

HCID 700065644-[(2S)-3-(2-{4-[2-(2-Cyclopentyl-ethyl)-imidazo[4,5-b]pyridin-3-yl]-phenyl}-ethylamino)-2-hydroxy-propoxy]-phenolYield 77.7%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

(2S)-1-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-3-({4-[2-(2-cyclopentylethyl)-3H-imidazo[4,5-b]pyridin-3-yl]phenethyl}amino)-2-propanol (0.209 g, 0.283 mmol) was reacted according to Procedure H (eluant: 10:1 going to 5:1 chloroform-methanol containing 1% ammonium hydroxide) to give the title compound (0.11 g, 0.22 mmol).

Sources & evidence

ORD record
ord-bd3ddf9baad343c98627f34ee9046650
Source dataset
uspto-grants-2003_03
Patent number
US06537994B2

Reaction notes

Loading…