Diisopropylethylamine → 1,1-Dimethylethyl 3-[5-(5-{3-cyano-4-[(2,2,2-trifluoroethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate

Participants

Reaction Conditions

Reaction Steps

3-Cyano-4-[(2,2,2-trifluoroethyl)oxy]benzoic acid (D29; 0.171 g, 0.698 mmol) was stirred in DMF (4.5 ml) with HATU (0.318 g, 0.837 mmol) and DIPEA (0.366 ml, 2.093 mmol) at room temperature for 20 mins. 1,1-Dimethylethyl 3-{5-[(hydroxyamino)(imino)methyl]-1-isoquinolinyl}propanoate (D36, 0.22 g, 0.698 mmol) was added and the resulting mixture was heated to 120° C. for 30 mins in a Biotage Initiator microwave. The solvent was removed under vacuum and diethyl ether was added to the residue to give a colourless solid. Methanol was added to dissolve the brown oil remaining and the mixture filtered. A white solid was collected, which was dried in a vacuum oven to give the title compound as a white solid (164 mg).

Provenance & Evidence