반응 #48432

반응 방정식

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

수율 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

수율 83.0%

용매

tetrahydrofuran

dichloromethane

반응 조건

후처리

1. 1
   workup.WAITAfter 18 h
2. 2
   추출the mixture was extracted with ethyl acetate
3. 3
   세척The organic layer was washed with saturated aqueous sodium carbonate (3×), saturated brine
4. 4
   건조dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타Purification by silica gel chromatography (100% dichloromethane→93% dichloromethane/methanol)

실험 절차

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).

출처