1-Aminopiperidine → 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfanyl-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide

To a magnetically stirred suspension of 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfanyl-1H-imidazole-4-carboxylic acid (1.72 g, 4.16 mmol) in anhydrous CH3CN (45 ml) was successively added N,N-diisopropylethylamine (Hunig's base) (1.60 ml, 9.20 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (1.89 g, 4.99 mmol) and 1-aminopiperidine (0.54 ml, 5.01 mmol). After stirring for 40 h, water was added and the resulting mixture was extracted with dichloromethane. The dichloromethane layer was successively twice washed with an 1N HCl solution and water, dried over MgSO4, filtered and concentrated to give a crude oil. This oil was further purified by flash chromatography (silicagel, EtOAc) and triturated with diethyl ether to give 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfanyl-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide in 72% yield, mp 170° C. (dec);

1. extractionthe resulting mixture was extracted with dichloromethane
2. washThe dichloromethane layer was successively twice washed with an 1N HCl solution and water
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a crude oil
7. customThis oil was further purified by flash chromatography (silicagel, EtOAc)
8. customtriturated with diethyl ether

ORD record

ord-a43c986dd2844ec9a35a05da2dac0891

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07524867B2