Lithium borohydride → HCID 59291785, compound

Participants

Reaction Steps

Methyl 2-(6-(3-(8-acetyl-8-azabicyclo[3.2.1]octan-3-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-methylpyridin-3-yloxy)pyridin-3-ylthio)acetate (Prepared in Example 174, step d; 210 mg, 0.388 mmol) was dissolved in THF (4 mL) and LiBH4 (194 μL, 0.194 mmol) was added and stirred at ambient temperature for 30 minutes The reaction was cooled to 0° C. and LiAlH4 (194 μL, 0.194 mmol) was added and stirred for 20 minutes. The reaction was quenched with water and sodium sulfate, stirred for 10 minutes, filtered and concentrated. The residue was purified on silica gel (10% methanol in EtOAc) followed by reverse phase chromatography (5 to 95% ACN in water with 0.1% TFA) to afford 1-(3-(5-(5-(2-hydroxyethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)ethanone (52.5 mg, 0.102 mmol, 26.4% yield) as a solid after converting the salt to the free base. Mass spectrum (apci) m/z=513.2 (M+H).

Provenance & Evidence