1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53246995, compound

Participants

Reaction Steps

To a suspension of 1-[(1-ethyl-1H-1,2,3-triazol-4-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione trifluoroacetate (250 mg; compound B47), 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (180 mg; compound C10), EDCI (174 mg) and HOBT hydrate (123 mg) in DCM (12 ml) DIPEA (0.24 ml) is added. After 1.5 h at RT additional 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (100 mg; compound C10) is added and the reaction mixture is stirred for additional 5 d at RT. Aqueous potassium hydrogen sulfate solution (10% w/w) is added and the mixture is filtered using a phase separator. The organic layer is concentrated under reduced pressure and the residue is purified by flash column chromatography [silica gel, eluent: DCM/MeOH, 95/5 (v/v)] to afford the title compound as a solid.

Provenance & Evidence