4-Methylmorpholine → N-[1-(4-cyano-3-fluoro-phenyl)-3-cyclopropyl-1-(3-methyl-3H-imidazol-4-yl)-prop-2-ynyl]-3-(3-methoxy-benzenesulfonylamino)-propionamide

Participants

Reaction Steps

(+)-4-[1-Amino-1-(3-(cyclopropylethynyl)-3H-imidazol-4-yl)-ethyl]-2-fluoro-benzonitrile bishydrochloride (0.120 g, 0.408 mmol), 3-(3-methoxy-benzenesulfonylamino)-propionic acid (Example 7, Step B) (0.1273 g, 0.49 mmol), Bop reagent (0.186 g, 0.49 mmol), 1-hydroxy-7-aza-benzotriazole (HOAT) (0.067 g, 0.49 mmol) and N-methyl morpholine(0.134 mL, 1.22 mmol) were dissolved in DMF (5.0 mL) and stirred for 18 h. The reaction mixture was concentrated in vacuo, partitioned between EtOAc and saturated NaHCO3 solution, the organic layer separated, washed with H2O, brine, and dried (MgSO4). Filtration and concentration in vacuo gave the title compound after chromatography on an ISCO Combiflash eluting with 2-5% MeOH/CH2Cl2 with NH4OH. MS (M+1) 536.

Provenance & Evidence