反応 #72011

反応方程式

Ethyl acetate

cis(±)-4-chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

(1-cyclopropyl-7-fluoro-8-methoxy-4-oxo-1,4-dihydroquinolin-3-yl)carbonyl difluoroborate

→

title compound

収率 62.0%

cis(±)-7-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-1-cyclopropyl-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

収率 62.0%

溶媒

Triethylamine

triethylamine

water

Ethanol

DMSO

反応条件

後処理

1. 1
   洗浄the organic layer was washed with saturated aqueous sodium bicarbonate solution
2. 2
   乾燥dried over anhydrous sodium sulfate
3. 3
   濃縮concentration under reduced pressure
4. 4
   workup.STIRRINGthe mixture was stirred at 80° C. for six hours
5. 5
   温度The reaction solution was cooled to room temperature
6. 6
   ろ過The resulting solid was collected by filtration
7. 7
   洗浄washed with ethanol

実験手順

Ethyl acetate was added to cis(±)-4-chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (100 mg, 0.297 mmol), and the organic layer was washed with saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue and (1-cyclopropyl-7-fluoro-8-methoxy-4-oxo-1,4-dihydroquinolin-3-yl)carbonyl difluoroborate obtained in Example (146a) (82 mg, 0.30 mmol) were dissolved in DMSO (0.6 mL). Triethylamine (0.100 mL, 0.721 mmol) was added, and the mixture was stirred at 40° C. overnight. Ethanol (3 mL), water (0.3 mL) and triethylamine (0.3 mL) were added to the reaction solution, and the mixture was stirred at 80° C. for six hours. The reaction solution was cooled to room temperature. The resulting solid was collected by filtration and washed with ethanol to obtain 102.5 mg of the title compound as a pale yellow solid (62%).

出典