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

Participants

Reaction Steps

One droplet of DMF was added to a solution of 7-(4-butoxyethoxyphenyl)-1-[(2-methylthiazol-4-yl)methyl]-2,3-dihydro-1-benzazepine-4-carboxylic acid (150 mg) in chloroform (10 ml). Then, thionyl chloride (47 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 (87 mg) and triethylamine (800 mg) in chloroform (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) to give 7-(4-butoxyethoxyphenyl)-1-[(2-methylthiazol-4-yl)methyl]-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 76) (37 mg) as yellow amorphous.

Provenance & Evidence