Tetrahydrofuran → HCID 178467897, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 1-[5-(2,4-difluorophenyl)-4-[2-[[(1S)-2-ethoxy-1-methyl-ethyl]amino]oxazolo[5,4-b]pyridin-5-yl]-1H-imidazol-2-yl]cyclopropanecarboxylate (0.9 g, 1.99 mmol) is dissolved in dry diethyl ether (20 mL) and dry THF (7 mL) under a nitrogen atmosphere and cooled to 0° C. Lithium borohydride (87 mg, 3.99 mmol) is added portionwise and the mixture stirred at 0° C. for 1 h. The remaining reactants are quenched by adding 1 N HCl until pH=1 to the mixture at RT dropwise for 30 min. The mixture is washed with ethyl acetate, the aqueous layer basified (until pH=8) with NaOH, and extracted with dichloromethane. The combined organic layers are dried over MgSO4, filtered, and concentrated under reduced pressure. The residue is purified by normal phase chromatography (120 g silica-gel cartridge) using a gradient of hexane-ethanol to afford the title compound (0.56 g, 60%). LC-ES/MS m/z 470.2 (M+1); [α]D22−18.00°, (c=0.50, MeOH); [α]D22−18.0°, (c=0.50, CHCl3).

Provenance & Evidence