9-(5-Phenylthiophen-2-yl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide → 9-(5-Phenylthiophen-2-yl)-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

A mixture of 10% palladium-carbon (50% wet, 12 mg) and 9-(5-phenylthiophen-2-yl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (120 mg) in ethanol (10 mL) and dehydrated THF (60 mL) was stirred under a hydrogen atmosphere at room temperature for 4 hr. To the reaction mixture was added 5% rhodium-carbon (50% wet, 12 mg) and the mixture was stirred under a hydrogen atmosphere at room temperature overnight, and under a hydrogen atmosphere (4 atm) for 6 hr. To the reaction mixture was added 5% ruthenium-alumina (12 mg) and the mixture was stirred under a hydrogen atmosphere at room temperature overnight. To the reaction mixture was added platinum dioxide (12 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 24 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by aminopropyl silica-bound silica gel column chromatography (ethyl acetate/methanol) to give the title compound (42.3 mg) as a white solid. The obtained solid was crystallized from acetonitrile and diisopropyl ether.

1. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature overnight
2. waitunder a hydrogen atmosphere (4 atm) for 6 hr
3. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature overnight
4. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature for 24 hr
5. filtrationThe reaction mixture was filtered through celite
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe residue was purified by aminopropyl silica-bound silica gel column chromatography (ethyl acetate/methanol)

ORDレコード

ord-8abe15c15b614a22bf6953ac4805a74d

出典データセット

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08916551B2