Ethanolamine → 2-({[5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazol-2-yl]methyl}amino)ethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazole-2-carbaldehyde (300 mg) in methanol (10 mL) was added 2-aminoethanol (250 μL) at room temperature, and the mixture was stirred at 80° C. for 1 hr. The reaction mixture was cooled to room temperature, sodium tetrahydroborate (72 mg) was added to the reaction mixture, and the mixture was stirred at room temperature for 30 min. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to basic silica gel column chromatography to give a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-methanol (9:1, volume ratio). The pale-yellow amorphous solid was subjected to silica gel column chromatography, and the title compound (188 mg, yield 57%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-methanol (8:2, volume ratio). MS: 517 (MH+).

Provenance & Evidence