Diisopropylethylamine → Tert-butyl 4-(2-chloro-4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)butanoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-cyclopentyl-6-methoxy-isonicotinic acid (33 mg, 0.149 mmol), TBTU (50 mg, 0.156 mmol) and DIPEA (62 mg, 0.479 mmol) in DMF (2 mL) is stirred at rt for 15 min before tert-butyl 4-(2-chloro-4-(N-hydroxycarbamimidoyl)-6-methylphenoxy)butanoate (51 mg, 0.149 mmol) is added. The mixture is stirred at rt for 1 h before another portion of TBTU (50 mg, 0.156 mmol) is added. Stirring is continued at rt for 2 h. The mixture is heated to 110° C. and stirring is continued for another hour. The mixture is concentrated and the crude product is purified by prep. HPLC to give tert-butyl 4-(2-chloro-4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-6-methylphenoxy)butanoate (33 mg) as a colourless glass; LC-MS: tR=1.28 min, [M+H]+=528.37.

Provenance & Evidence