Ammonium Chloride → 3-{3'-[(3-Methanesulfonyl-5-trifluoromethyl-benzoyl)-methyl-amino]-[3,4']bipyridinyl-2-yloxy}-azetidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

To a solution of tert-butyl 3-(3′-(methylamino)-3,4′-bipyridin-2-yloxy)azetidine-1-carboxylate (0.149 g, 418 μmol) in CH2Cl2 (4 mL) were added 3-(methylsulfonyl)-5-(trifluoromethyl)benzoyl chloride (240 mg, 836 μmol, example 223, intermediate d) and DIPEA (216 mg, 292 μL, 1.67 mmol) and the light yellow solution was stirred at room temperature for 24 hours. Another batch of 3-(methylsulfonyl)-5-(trifluoromethyl)benzoyl chloride (164 mg, 573 μmol) and DIPEA (162 mg, 219 μL, 1.25 mmol) was added and stirring was continued at room temperature for 24 hours. The reaction mixture was poured on saturated aqueous NH4Cl solution and CH2Cl2 and the layers were separated. The aqueous layer was extracted three times with CH2Cl2. The organic layers were dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was twice purified by silica gel chromatography on a 20 g column using an MPLC system eluting with EtOAc. Light yellow gum (0.105 g; 41%). MS (ESI): m/z=607.18 [M+H]+.

Provenance & Evidence