4-Methylmorpholine → 1-Isopropyl-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid (5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-amide

Participants

Reaction Steps

A solution of 1-isopropyl-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid (preparation 3, 65 mg, 0.192 mmol), TBTU (75 mg, 0.232 mmol), N-methylmorpholine (42 μL, 0.383 mmol) in DMF (1 mL) is stirred for 15 min at room temperature. C-(5-Methyl-[1,3,4]oxadiazol-2-yl)-methylamine (24 mg, 0.211 mmol) is added and the reaction mixture is stirred for 18 h at room temperature. The reaction mixture is purified by preparative reversed-phase HPLC (Sunfire, gradient of acetonitrile in water, 0.1% TFA, 60° C.). Yield: 6 mg (7% of theory); ESI mass spectrum: [M+H]+=435; Retention time HPLC: 0.86 min (Z018_S04).

Provenance & Evidence