Diisopropylethylamine → 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-[(1-methyl-1H-1,2,4-triazol-3-yl)methyl]-6-phenylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Steps

To a suspension of 1-[(1-methyl-1H-1,2,4-triazol-3-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride (249 mg, compound B92), 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (210 mg; compound C10) and HATU (267 mg) in DCM (7.0 ml) is added DIPEA (0.28 ml). The reaction mixture is stirred at RT for 14 h. Aqueous potassium bisulfate solution (10% w/w, 10 ml) is added and the mixture is extracted with DCM. After filtration using a phase separator the organic layer is concentrated under reduced pressure and the residue is purified by preparative HPLC to yield the title compound as a solid.

Provenance & Evidence