Diisopropylethylamine → 5-chloro-4-{[(5-chloro-6-cyclopropylpyridin-3-yl)oxy]methyl}-N-[(3,3-difluoroazetidin-1-yl)sulfonyl]-2-fluorobenzamide

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Reaction Steps

To a solution of 5-chloro-4-(((5-chloro-6-cyclopropylpyridin-3-yl)oxy)methyl)-2-fluorobenzoic acid (Preparation 27, 100 mg, 0.28 mmol) and 3,3-difluoroazetidine-1-sulfonamide (Preparation 23, 75 mg, 0.42 mmol) in DCM (10 mL) was added diisopropylethylamine (73 mg, 0.56 mmol) followed by 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (160 mg, 0.42 mmol). The mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. The residue was dissolved in DMSO (2 mL) and purified by reverse phase chromatography (0-90% acetonitrile/water containing 0.1% formic acid) to give the title compound as colourless solid (51 mg, 36%).

Provenance & Evidence