Methyl iodide → 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-methoxyethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

Sodium hydride (60 wt % in mineral oil) (50 mg, 1.25 mmol) was added to an ambient temperature solution of 4-(2,2-dimethylpropyl)-2-[1-hydroxy-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide in N,N-dimethylformamide (for synthesis see example 11) (2 mL). After stirring at ambient temperature for 20 min, methyl iodide (50 μL, 0.8 mmol) was added. After stirring at ambient temperature for a further 2 h, the reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with diethyl ether. The combined ethereal layers were dried (magnesium sulfate) and concentrated in vacuo to afford 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-methoxyethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide which was used in the subsequent step without further purification.

1. stirringAfter stirring at ambient temperature for a further 2 h
2. customthe reaction mixture was quenched with saturated aqueous ammonium chloride
3. extractionextracted with diethyl ether
4. dry with materialThe combined ethereal layers were dried (magnesium sulfate)
5. concentrationconcentrated in vacuo

ORD-Eintrag

ord-b87e67d3b4634f03b5883db9e76a6db8

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08106070B2