Reaction #42671

Reaction equation

Triethylamine

tert-butyl (3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-ylcarbamate

4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carbonyl chloride

→

title compound

Yield 84.5%

N-[(3R,6S)-6-(2,3-Difluorophenyl)-2-thioxoazepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide

Yield 84.5%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Temperaturethe mixture heated to reflux
2. 2
   Concentrationconcentrated
3. 3
   OtherPurification by silica gel chromatography (100% dichloromethane o 95% dichloromethane/methanol)

Procedure

Triethylamine (0.45 mL, 3.25 mmol) was added to a solution of tert-butyl (3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-ylcarbamate (416 mg, 1.62 mmol) and 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carbonyl chloride (466 mg, 1.66 mmol) in dichloromethane (70 mL) and the mixture heated to reflux. After 18 h, the mixture was allowed to cool to ambient temperature and concentrated. Purification by silica gel chromatography (100% dichloromethane o 95% dichloromethane/methanol) gave the title compound (685 mg). MS 501.0 (M+1).

Source