1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[1-({4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]phenyl}carbonyl)piperidin-4-yl]-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-6-(4-fluorophenyl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Steps

1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-6-(4-fluorophenyl)-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride (310 mg; compound B87) is reacted with 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (216 mg; compound C10) and HOBt (83 mg) and EDCI (104 mg) in DMF (10 ml) according to the procedure described in example 46 to afford the title compound after purification by flash column chromatography [amino phase silica gel, eluation gradient: DCM/ethanol, 100/0/to 90/10 (v/v)] and by preparative HPLC as a solid.

Provenance & Evidence