Diisopropylethylamine → 3-[1-({3-[(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-phenylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Steps

The title compound is prepared analogously as described for example 1 using 3-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (159 mg; compound C8), 1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-6-phenyl-3-piperidin-4-ylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride (190 mg; compound B32), HBTU (167 mg), DIPEA (0.28 ml) and DCM (3 ml). The crude product is purified by flash column chromatography (amino phase silica gel, eluent gradient: EtOAc/methanol, 98/2 to 95/5 (v/v)) and afterwards by preparative TLC [silica gel, eluent: EtOAc/MeOH/triethylamine, 92.5/5/2.5 (v/v/v)] to yield the title compound as a solid.

Provenance & Evidence