Imidazole → HCID 178463970, Verbindung

HRID 25618

Reaktionsgleichung

[CH2:1]([N:3]([CH2:30][CH2:31][OH:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]([CH3:29])[S:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:11][CH2:10]1)[CH3:2].N1C=CN=C1.[CH3:38][C:39]([Si:42](Cl)([CH3:44])[CH3:43])([CH3:41])[CH3:40].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CN(C=O)C>[C:39]([Si:42]([CH3:44])([CH3:43])[O:32][CH2:31][CH2:30][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]([CH3:29])[S:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)(=[O:17])=[O:18])[CH2:11][CH2:10]1)([CH3:41])([CH3:40])[CH3:38]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

400 mg (8.4 mmol) trans-N-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide were suspended in toluene and evaporated (3×), redissolved in lml DMF and treated with 102.4 mg (1.5 mmol, 1.8 eq) imidazole. At 0° C., 176 mg (11.7 mmol, 1.4 eq) TBDMSCl in 2 ml DMF were added, and the reaction mixture was stirred at 50° C. for 1 h. The solution was added to an aqueous solution of NaHCO3 and extracted with ether. The organic layer was washed with water and brine, and dried over Na2SO4. 509 mg crude trans-N-[4-(5-{[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-ethyl-amino}-pentyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide were isolated as light yellow oil.

Aufarbeitung

customevaporated (3×)
dissolutionredissolved in lml DMF
extractionextracted with ether
washThe organic layer was washed with water and brine
dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag: ord-cc39c75da0944473b4915be6d02ba9a7
Quelldatensatz: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06858651B2

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