Dimethylformamide → 7-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-5-yl)amino]methyl]phenyl]-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxamide

One droplet of DMF was added to a solution of 7-(4-butoxyethoxyphenyl)-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (100 mg) in dichloromethane (10 ml). Then, thionyl chloride (31 mg) was added at 0° C., the temperature was returned to room temperature, and the mixture was stirred under nitrogen atmosphere for 1 hour. Then, this solution was added to a solution of 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (57 mg) and triethylamine (520 mg) in dichloromethane (20 ml) at 0° C. The mixture was stirred under nitrogen atmosphere at room temperature overnight, to the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was separated and purified with silica gel column chromatography (methanol:ethyl acetate=1:3), which was recrystallized hexane-ethyl acetate to give 7-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-5-yl)amino]methyl]phenyl]-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 78) (43 mg) as colorless crystals.

1. customwas returned to room temperature
2. stirringThe mixture was stirred under nitrogen atmosphere at room temperature overnight, to the mixture
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialdried with magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe resulting residue was separated
8. custompurified with silica gel column chromatography (methanol:ethyl acetate=1:3), which
9. customwas recrystallized hexane-ethyl acetate

ORDレコード

ord-351416825502438eb6c39306fde31311

出典データセット

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06936602B1