Cyclopentanemethanol → N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]-8-(cyclopentylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxamide

HRID 64459

Reaktionsgleichung

[Si:1]([O:8][CH2:9][C@H:10]([NH:17][C:18]([C:20]1[N:24]2[CH:25]=[CH:26][CH:27]=[C:28]([OH:29])[C:23]2=[N:22][C:21]=1[CH3:30])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:31]1([CH2:36]O)[CH2:35][CH2:34][CH2:33][CH2:32]1.C(P(=CC#N)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9][C@H:10]([NH:17][C:18]([C:20]1[N:24]2[CH:25]=[CH:26][CH:27]=[C:28]([O:29][CH2:36][CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[C:23]2=[N:22][C:21]=1[CH3:30])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of 120 mg of N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]-8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxamide, 60 μl of cyclopentylmethanol, 156 μl of (tributylphosphoranylidene)acetonitrile, and 2.4 ml of toluene was stirred at 110° C. for 16 hours, followed by purification using silica gel chromatography, to obtain 100 mg of N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]-8-(cyclopentylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Aufarbeitung

customfollowed by purification

Quellen und Nachweise

ORD-Eintrag: ord-5ab65197b73f4c0aac187c473560d72d
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09447090B2

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