Potassium Hydroxide → HCID 67350841, compound

Participants

Reaction Steps

A solution of 4-amino-2′-methyl-6′-(pyrrolidine-1-carbonyl)biphenyl-3-carbaldehyde (0.100 g, 0.324 mmol) in DMSO (3.0 mL) was added to an 80° C. solution of 2-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)acetonitrile (0.067 g, 0.486 mmol) and potassium hydroxide (0.016 g, 0.28 mmol) (11 M aq., 44 uL) in DMSO (1.25 mL) in 4 portions at 15 min intervals. The resulting mixture was heated for 18 h, cooled, filtered and purified by prep HPLC (12-51% CH3CN/water, 0.1% TFA) to give (2-(2-amino-3-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone as a yellow solid. MS (ESI, pos. ion) m/z: 429 (M+1).

Provenance & Evidence