1,2-Dichloroethane → N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-N'-[(2S,3R)-1-(3,5-difluorophenyl)-4-[[1-(3-ethylphenyl)cyclopropyl]amino]-3-hydroxybutan-2-yl]pentanediamide;formic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of R-aminoqtuinuclidine (0.084 g, 0.421 mmol) TEA (0.294 ml, 2.11 mmol), and anhydrous DMF (2.5 ml) was added 5-[((1S,2R)-1-(3,5-difluorobenzyl)-3-{[1-(3-ethylphenyl)cyclopropyl]amino}-2-hydroxypropyl)amino]-5-oxopentanoic acid (0.200 g, 0.421 mmol), EDC (0.121 g, 0.632 mmol), HOBT (0.085 g, 0.632 mmol) under nitrogen, with stirring at 45° C. overnight. Reaction mixture was quenched with 10% sodium bicarbonate (aq.) then extracted with ethyl acetate then concentrated in vacuo, yielding product (0.122 g). Prep-HPLC yielded the product as its formate salt. (ES+: 583.3)

Provenance & Evidence