Methylamine → 5-(4-chlorophenyl)-6-cyclohexyl-N-methyl-4-(2-morpholin-4-yl-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxamide

Beteiligte Stoffe

Reaktionsschritte

A solution (0.02 M) of 5-(4-chlorophenyl)-6-cyclohexyl-4-(2-morpholin-4-yl-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acid in DCM at RT was treated with methylamine (2 N solution in THF, 1.5 eq.), DIEA (3 eq.) and HATU (2 eq.). The mixture was stirred at RT for 2 h, then it was diluted with DCM and washed sequentially with aqueous HCl (0.1 N), aqueous NaHCO3 (saturated solution) and dried. Evaporation of the solvent under reduced pressure gave a residue which was purified by RP-HPLC (Conditions: Waters X-TERRA MS C18, 10 micron, 19×100 mm; flow: 20 mL/min; Gradient: A: H2O+0.05% TFA; B: MeCN+0.05% TFA; 50% A isocratic for 1 min then linear to 20% A in 9 min) to afford the title compound (74%) as a solid.

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