Phosgene → n-[(3r,7r)-1-(Cyclopropylmethyl)-2-oxo-7-phenylazepan-3-yl]-4-(2-oxo-4-phenyl-2,3-dihydro-1h-imidazol-1-yl)piperidine-1-carboxamide

Diisopropylethylamine (0.020 mL, 0.11 mmol) and phosgene (0.06 mL, 0.56 mmol) were added to a solution of 4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)piperidinium chloride (27 mg, 0.111 mmol) in dichloromethane (1 mL) at 0° C. After 30 min, the mixture was concentrated in vacuo and azeotroped with dichloromethane (2×) to give the crude amine. Diisopropylethylamine (0.04 ml, 0.22 mmol) was added to a solution of the crude amine and (3R,7R)-3-amino-1-(cyclopropylmethyl)-7-phenylazepan-2-one (28.7 mg, 0.11 mmol) in dichloromethane (1 mL) and the mixture heated to reflux. After 15 min, the mixture was concentrated and purified by silica gel chromatography (1% methanol/dichloromethane—5% methanol/dichloromethane) gave the title compound (38 mg). MS 528.3 (M+1).

1. concentrationthe mixture was concentrated in vacuo
2. customazeotroped with dichloromethane (2×)
3. customto give the crude amine
4. temperaturethe mixture heated to reflux
5. waitAfter 15 min
6. concentrationthe mixture was concentrated
7. custompurified by silica gel chromatography (1% methanol/dichloromethane—5% methanol/dichloromethane)

ORDレコード

ord-41494fcac4b646c5975656cafba9334e

出典データセット

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07491713B2