Diisopropylcarbodiimide → HCID 178467898, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 1-[4-(5-amino-6-hydroxy-2-pyridyl)-5-(2,4-difluorophenyl)-1H-imidazol-2-yl]cyclopropanecarboxylate (4 g, 10.35 mmol) and (2S)-1-ethoxy-2-isothiocyanato-propane (2.379 g, 15.53 mmol) are dissolved in ethanol (34 mL). The mixture is heated to 85° C. in a sealed flask for 16 h. Diisopropyl carbodiimide (3.21 g, 20.71 mmol) is added dropwise and the mixture is stirred at 85° C. for 16 h, after which time an additional 3 g of diisopropyl carbodiimide is added and the mixture is heated at 85° C. for an additional 4 h. The solvent is evaporated and the residue is purified by normal phase chromatography (120 g silica-gel cartridge, using a hexane-ethanol gradient to afford the title compound (1.180 g, 24%). LC-ES/MS m/z 498.1 (M+1).

Provenance & Evidence