Diisopropylethylamine → 2-{2-[5-(4-chloro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-N-methyl-acetamide

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Reaction Steps

The 2-(2-formyl-phenoxy)-N-methyl-acetamide (0.0311 mmol) is added to 4-chloro-thiobenzoic acid hydrazide (0.0342 mmol) in 0.1 mL of CH2Cl2. After 10 minutes, DIEA (0.05 mL) and 2,4,6-trifluoro-benzoyl chloride (0.0467 mmol) are added. The mixture is kept at room temperature overnight. After removal of solvent, the residue is purified by preparative HPLC (20-100% MeCN/H2O gradient) to give the product 2-{2-[5-(4-chloro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-N-methyl-acetamide as an off white solid: LC/MS (ES+): 520.1 (M+1)+.

Provenance & Evidence