Diisopropylcarbodiimide → HCID 178495114, compound

Participants

Reaction Conditions

Reaction Steps

A KIMAX® tube is charged with 3-amino-6-[5-(2,4-difluorophenyl)-2-(3-methyloxetan-3-yl)-1H-imidazol-4-yl]pyridin-2-ol (2.28 g, 6.36 mmol) and ethanol (18 mL). (3S)-3-Isothiocyanato-1-methoxy-butane (1.39 g, 9.54 mmol) is added, the flask sealed, and the mixture is heated to 85° C. After 16 h, (3S)-3-isothiocyanato-1-methoxy-butane (700 mg) is added and the mixture is stirred for 48 h at 85° C. in the sealed tube. N,N′-diisopropylcarbodiimide (1.04 g) is added and the mixture is stirred 3 h at 85° C. in the sealed tube. The crude reaction mixture is concentrated under reduced pressure and the residue purified by normal phase chromatography (120 g silica-gel cartridge, hexane-ethanol). The desired compound elutes at 3% of ethanol to give the title compound as a brown solid (2.61 g, 87%). LC-ES/MS m/z 470 (M+1); [α]D22+42.2°, (c=0.50, methanol).

Provenance & Evidence