Triethylamine → HCID 70663289, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cold solution of N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-3-(2-hydroxyethylthio)-N-methyl-5-(trifluoromethyl)benzamide (0.16 g, 333 μmol, example 216) in CH2Cl2 (2 mL) were added triethylamine (50.5 mg, 69.6 μL, 500 μmol) and methanesulfonyl chloride (38.1 mg, 25.8 μL, 333 μmol) and the clear colorless solution was stirred at 0° C. for 3.75 hours. The reaction mixture was poured on saturated aqueous NaHCO3 solution and CH2Cl2 and the layers were separated. The aqueous layer was extracted twice with CH2Cl2. The organic layers were washed once with brine, dried over MgSO4, filtered, and evaporated. The intermediate mesylate was dissolved in isopropylacetate (2.0 mL), treated with azetidine (41.8 mg, 49.4 μL, 733 μmol) and heated to reflux (oil bath 95° C.) for 16 hours. The reaction mixture was poured on saturated aqueous NH4Cl solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were dried over MgSO4, filtered and evaporated. The product was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Colorless solid (0.055 g; 31%). MS (ESI): m/z=520.17 [M+H]+.

Provenance & Evidence