Diisopropylethylamine → HCID 53246621, compound

Participants

Reaction Steps

To a suspension of 1-({3-[(methylsulfanyl)methyl]-1,2,4-oxadiazol-5-yl}methyl)-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride (202.4 mg; compound B36), 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (159 mg; compound C10) and HBTU (167 mg) in DCM (8 ml) is added DIPEA (207 mg). The reaction mixture is stirred for 3 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 (80 mg; compound C10) and HBTU (84 mg) are added in order to complete the reaction. A saturated aqueous sodium bicarbonate solution (5 ml) is added and the mixture is extracted with DCM (25 ml). The phases are separated and the aqueous phase is extracted with further DCM (10 ml). The organic phases are combined and filtered using a phase separator. The organic layer is concentrated under reduced pressure and the residue is purified two times by flash column chromatography [amino phase silica gel, eluation gradient: cyclohexane/EtOAc, 100/0 to 0/100 (v/v)] to yield the title compound as a solid.

Provenance & Evidence