Hydrochloric Acid → HCID 178495116, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-[5-(2,4-difluorophenyl)-4-[2-[[(1S)-3-methoxy-1-methyl-propyl]amino]oxazolo[5,4-b]pyridin-5-yl]-1H-imidazol-2-yl]-2-methyl-propanoate (50 g, 100.1 mmol) is dissolved in a mixture of diethyl ether (1 L) and THF (500 mL). The mixture is cooled to 0° C. and lithium borohydride (4.36 g, 200.19 mmol) is added. The reaction mixture is stirred at RT under a nitrogen atmosphere for 2 h. 1 M HCl (600 mL) is slowly added (gas evolution) and the resulting mixture is stirred for 1.5 h at RT. The layers are separated and the aqueous phase is extracted with methyl tert-butyl ether. The aqueous layer is basified (pH=8) by the addition of 2 M NaOH (200 mL) and is extracted with dichloromethane (3×400 mL). The combined organic layers are dried over Na2SO4, filtered, and concentrated under reduced pressure to a brown foam. The crude is eluted through a silica gel column (eluent: dichloromethane/3N NH3 in methanol 95:5) to obtain the desired product as a violet colored foam (35 g). The solid is suspended in a mixture of 2:1 heptane/methyl tert-butyl ether and sonicated. The suspension is stirred at RT overnight. The solid is filtered and dried under a vacuum to afford the title compound as a crystalline off-white solid (30 g, 64%). MS (m/z): 472 (M+1).

Provenance & Evidence