Hydrochloric Acid → 6-cyclohexyl-3-[(dimethylamino)methyl]-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Following the procedure described above for [2-carboxy-6-cyclohexyl-4-(methoxymethyl)-5-phenyl-4H-thieno[3,2-b]pyrrol-3-yl]-N-[(1,1-dioxidotetrahydro-3-thienyl)methyl]methanaminium trifluoroacetate (step 4), treatment of a solution (0.03 M) of 6-cyclohexyl-3-formyl-4-(methoxymethyl)-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid in 1,2-dichloroethane with dimethylamine (2 M solution in THF, 1.2 eq.) and sodium triacetoxyborohydride (1.5 eq.) gave a residue that was dissolved in THF. The resulting solution (0.1 M) was treated with aqueous of HCl (1 N, 8 eq.) and the mixture was heated to 60° C. for 26 h. After cooling down, the mixture was concentrated to give a residue that was purified by RP-HPLC (Conditions: Waters X-TERRA MS C18, 10 micron, 19×150 mm; flow: 20 mL/min; Gradient: A: H2O+0.05% TFA; B: MeCN+0.05% TFA; 90% A isocratic for 2 min then linear to 10% A in 9 min) to afford the title compound (29%) as its TFA salt.

Provenance & Evidence