2-Methoxyethanol → HCID 67005395, compound

Participants

Reaction Conditions

Reaction Steps

In an inert atmosphere, N—[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-(6-bromo-pyridin-3-ylmethyl)-3-(4-trifluoromethyl-phenyl)-acrylamide (80 mg, 0.116 mmol), was dissolved in dry toluene (3 mL) followed by the addition of 2-methoxy-ethanol (11.4 mg, 0.15 mmol), tris-(dibenzylideneaceton)-dipalladium (2.1 mg, 0.002 mmol), xanthphos (4 mg, 0.007 mmol) and sodium tert.-butoxide (16.7 mg, 0.174 mmol). The mixture was heated to 50° C. and stirring continued for 90 min. The reaction mixture was cooled to rt, brine (5 mL) was added and the product was extracted with EtOAc (3×4 ml). The combined organic layers were concentrated under reduced pressure and the residue was purified by prep. HPLC to give 38 mg (47%) of N—[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-[6-(2-methoxy-ethoxy)-pyridin-3-ylmethyl]-3-(4-trifluoromethyl-phenyl)-acrylamide. (LC-MS: tR=1.06 min; [M+H]+=687.27).

Provenance & Evidence