HCID 59234644, compound → HCID 66915773, compound

Participants

Reaction Conditions

Reaction Steps

TEA (0.056 ml, 0.4 mmol) was added to a solution of 1-(4-chlorobutyl)-6′-methyl-3,3′-bipyridin-2(1H)-one (55 mg, 0.2 mmol, Prep8) and (1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (Prep4, 70 mg, 0.31 mmol, reference procedure for preparation also reported in WO 2005080382) in anhydrous DMF (2 ml). The reaction mixture was heated at 90° C. for 1 hour and then at 100° C. for 24 hours, quenched with water and extracted with ethyl acetate. The combined organics layers were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by SCX cartridge (eluting with methanol followed by 2N ammonia solution in methanol) and then by SPE cartridge eluting with a gradient of methanol in DCM (from 0 to 5%) to afford the free base of the title compound (19 mg, 20%).

Provenance & Evidence