Ammonium Chloride → HCID 70663275, compound

Participants

Reaction Steps

To a suspension of N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-3-mercapto-N-methyl-5-(trifluoromethyl)benzamide (0.05 g, 115 μmol, Example 216, intermediate a) in acetonitrile (1 mL) were added 4-bromobutanoic acid (36.4 mg, 218 μmol) and DIPEA (29.6 mg, 40.0 μL, 229 μmol). After the addition of DIPEA the white suspension turned to a light yellow solution, which was stirred at room temperature for 24 hours before another batch of DIPEA (29.6 mg, 40.0 μL, 229 μmol) was added (white suspension turned into light yellow solution). The reaction mixture was stirred at room temperature for another 20 hours and then 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 (0.01 g; 16%). MS (ESI): m/z=523.13 [M+H]+.

Provenance & Evidence