Morpholine → HCID 11775339, compound

Participants

Reaction Steps

Following the procedure described above for 6-cyclohexyl-4-[2-(dimethylamino)-2-oxoethyl]-5-phenyl-4N-thieno[3,2-b]pyrrole-2-carboxylic acid (step 3), treatment of a solution (0.08 M) of [6-cyclohexyl-2-(methoxycarbonyl)-5-phenyl-4H-thieno[3,2-b]pyrrol-4-yl]acetic acid in DMF with morpholine (1.1 eq.), DIEA (3 eq.) and HATU (1.1 eq.) followed by treatment of a solution (0.1 M) of the resulting residue in DCM with BBr3 (1 M solution in DCM, 3 eq.) gave a residue that was purified by RP-HPLC (Conditions: Waters X-TERRA MS C18, 5 micron, 19×150 mm; flow: 17 mL/min; Gradient: A: H2O+0.05% TFA; B: MeCN+0.05% TFA; 60% A isocratic for 4 min, linear to 50% A in 2 min, linear to 40% in 2 min then isocratic for 2 min, linear to 35% A in 2 min isocratic for 1 min then linear to 30% A isocratic for 1 min then linear to 0% A in 3 min) to afford the title compound (43%) as a solid.

Provenance & Evidence