Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilane → 4-[(2S)-3-(2-{4-[2-(2-Cyclopentyl-ethyl)-imidazo[4,5-b]pyridin-3-yl]-phenyl}-ethylamino)-2-hydroxy-propoxy]-phenol

HRID 1862777Notes

Reaction equation

HRID 1862777 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8]2[N:16]([C:17]3[CH:25]=[CH:24][C:20]([CH2:21][CH2:22][NH2:23])=[CH:19][CH:18]=3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Si]([O:43][C:44]1[CH:49]=[CH:48][C:47]([O:50][CH2:51][CH:52]2[CH2:54][O:53]2)=[CH:46][CH:45]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>C(Cl)(Cl)Cl.CO>[CH:1]1([CH2:6][CH2:7][C:8]2[N:16]([C:17]3[CH:25]=[CH:24][C:20]([CH2:21][CH2:22][NH:23][CH2:54][C@H:52]([OH:53])[CH2:51][O:50][C:47]4[CH:48]=[CH:49][C:44]([OH:43])=[CH:45][CH:46]=4)=[CH:19][CH:18]=3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12045564Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilaneHCID 186196114-[2-(2-Cyclopentylethyl)-3H-imidazo[4,5-b]pyridin-3-yl]phenethylamine

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 43.1%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

4-[2-(2-Cyclopentylethyl)-3H-imidazo[4,5-b]pyridin-3-yl]phenethylamine (0.22 g, 0.658 mmol) was reacted with tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenyl-silane (0.266 g, 0.656 mmol) according to Procedure G (eluant: 20:1 going to 5:1 chloroform-methanol) to give the title compound (0.209 g, 0.283 mmol).

Sources & evidence

ORD record
ord-c5e47aafac6e4067b224baa525b02395
Source dataset
uspto-grants-2003_03
Patent number
US06537994B2

Reaction notes

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