Trifluoroacetic acid → HCID 117843117, compound

Participants

Reaction Conditions

Reaction Steps

The crude TFA salt of (R)-4-((R)-1-((3-(difluoromethyl)-6-(3-methoxy-4-(piperazin-1-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one: 3.67 (0.064 mmol) was dissolved in THF (1 mL) and iPr2NEt (12 μL, 0.07 mmol) was added followed by oxetan-3-one (18 μL, 0.30 mmol) and sodium triacetoxyborohydride (61 mg, 0.29 mmol). The reaction mixture was stirred at 50-55° C. for 18 h and was diluted with water, 5% (w/v) aqueous Na2CO3, and EtOAc. The phases were separated, and the aqueous phase was extracted with EtOAc. The combined organic phase was dried over Na2SO4, filtered, and concentrated to afford a crude residue that was purified by silica gel chromatography (0-20% MeOH in DCM) to yield (R)-4-((R)-1-((3-(difluoromethyl)-6-(3-methoxy-4-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (3.70).

Provenance & Evidence