1,1'-Carbonyldiimidazole → HCID 136387035, compound

Participants

Reaction Conditions

Reaction Steps

(2R,4S)-4-([3,5-Bis(trifluoromethyl)benzyl]-{5-[2-(N-hydroxy-carbamimidoyl)ethyl]pyrimidin-2-yl})amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (140 mg) is dissolved in acetonitrile (1 ml), and thereto is added carbodiimidazole (51 mg). The mixture is heated at 60° C. and stirred for 25.5 hours. The reaction solution is cooled to room temperature, and partitioned by adding water and ethyl acetate. The organic layer is washed with saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; chloroform:methanol=1:0→19:1) to give (2R,4S)-4-([3,5-bis-(trifluoromethyl)benzyl]-{5-[2-(5-oxo-4,5-dihydro[1,2,4]oxadiazol-3-yl)ethyl]pyrimidin-2-yl})amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (84 mg). MS (m/z): 696 [M+H]+.

Provenance & Evidence