反応 #48432

反応方程式

sodium carbonate

Triethylamine

(3R,6S)-3-amino-1-(2-methoxyethyl)-6-phenylazepan-2-one

4-nitrophenyl chloroformate

2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride

diisopropylethylamine

→

title compound

収率 83.0%

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

収率 83.0%

溶媒

tetrahydrofuran

dichloromethane

反応条件

後処理

1. 1
   workup.WAITAfter 18 h
2. 2
   抽出the mixture was extracted with ethyl acetate
3. 3
   洗浄The organic layer was washed with saturated aqueous sodium carbonate (3×), saturated brine
4. 4
   乾燥dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他Purification by silica gel chromatography (100% dichloromethane→93% dichloromethane/methanol)

実験手順

Triethylamine (0.015 mL, 0.107 mmol) was added to a solution of (3R,6S)-3-amino-1-(2-methoxyethyl)-6-phenylazepan-2-one (28 mg, 0.107 mmol) and 4-nitrophenyl chloroformate (22 mg, 0.107 mmol) in tetrahydrofuran (2 mL) at 0° C. After 30 min, 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride (37 mg, 0.128 mmol), diisopropylethylamine (0.074 mL, 0.427 mmol) and dichloromethane (2.5 mL) were added and the mixture allowed to warm to ambient temperature. After 18 h, saturated aqueous sodium carbonate was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium carbonate (3×), saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→93% dichloromethane/methanol) gave the title compound (45 mg). MS 507.2737 (M+1).

出典