تفاعل #48451

معادلة التفاعل

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

triethylamine

Triethylamine

(3R,6S)-3-amino-6-(2,3-difluorophenyl)-7-(hydroxymethyl)azepan-2-one

4-nitrophenyl chloroformate

→

title compound

المردود 15.7%

N-[(3R,6S)-6-(2,3-difluorophenyl)-7-(hydroxymethyl)-2-oxoazepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide

المردود 15.7%

المذيبات

chloroform

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated
2. 2
   workup.ADDITIONdiluted with saturated aqueous sodium bicarbonate
3. 3
   استخلاصextracted with dichloromethane (2×)
4. 4
   غسيلThe organic layer was washed with water, saturated brine
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىPurification by silica gel chromatography (1%→12% methanol/dichloromethane)

الإجراء التجريبي

Triethylamine (0.68 mL, 0.49 mmol) was added to a solution of (3R,6S)-3-amino-6-(2,3-difluorophenyl)-7-(hydroxymethyl)azepan-2-one (57 mg, 0.21 mmol) and 4-nitrophenyl chloroformate (47 mg, 0.23 mmol) in tetrahydrofuran (10 mL) at 0° C. After 30 min, 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride (98 mg, 0.34 mmol), triethylamine (0.84 mmol) and chloroform (10 mL) were added and the mixture allowed to warm to ambient temperature. The reaction was stirred overnight, concentrated, diluted with saturated aqueous sodium bicarbonate and extracted with dichloromethane (2×). The organic layer was washed with water, saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (1%→12% methanol/dichloromethane) gave the title compound (17 mg). MS 515.2203 (M+1).

المصدر