1-Hydroxybenzotriazole → 4-(dimethylamino)-N-((1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-1-naphthalenecarboxamide

To a solution of (1RS,2RS)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine (150 mg, 0.42 mmol) in acetonitrile (10 ml) were added 4-dimethylaminonaphthalenecarboxylic acid (89 mg, 0.42 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (119 mg, 0.62 mmol) and 1-hydroxy-1H-benzotriazole (63.6 mg, 0.42 mmol) and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (50 ml) and extracted with ethyl acetate (50 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) and recrystallized from ethyl acetate-hexane to give the title compound (149 mg, 70%).

1. extractionextracted with ethyl acetate (50 ml×2)
2. washThe extract was washed with saturated brine
3. dry with materialdried over anhydrous magnesium sulfate
4. customevaporated under reduced pressure
5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
6. customrecrystallized from ethyl acetate-hexane

ORDレコード

ord-2b3d5ac7bd7d42e9b4419cb1e27524d0

出典データセット

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06982348B2