1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53246994, compound

Participants

Reaction Steps

To a suspension of 1-[(3-ethyl-1,2,4-thiadiazol-5-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione trifluoroacetate (250 mg; compound B46), 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (175 mg; compound C10), EDCI (84 mg) and HOBT hydrate (60 mg) in DCM (15 ml) DIPEA (0.23 ml) is added. After 14 h at RT additional EDCI (84 mg) and HOBT hydrate (60 mg) are added and the reaction mixture is stirred for additional 3 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, eluation gradient: DCM/MeOH, 17/3 to 1/1 (v/v)] to afford the title compound as a solid.

Provenance & Evidence