Methyl iodide → HCID 86594357, compound

Participants

Reaction Steps

MeI (44 μL of a 2.3M solution in anhydrous DMF, 102 μmol) and K2CO3 (14 mg, 102 μmol) were added to a stirred solution of 3-cyclopentyl-2-(6-mercaptopyridin-3-yl)-N-thiazol-2-ylpropionamide (EXAMPLE 66, 34 mg, 102 μmol) in anhydrous DMF (1 mL). After 16 h, the solvents were evaporated off under reduced pressure, then the residue was partitioned between EtOAc (12 mL) and H2O (5 mL). The organic layer was washed with H2O (5 mL) and brine (5 mL), before being dried (MgSO4). The solution was filtered, passed through a short SiO2 plug, and evaporated to give 3-cyclopentyl-2-(6-methylsulfanylpyridin-3-yl)-N-thiazol-2-ylpropionamide: m/z (ES+)=348.2 [M+H]+. Step 2: Oxidation of this thioether (52 mg, 150 μmol), by the protocol described in EXAMPLE 55, gave the title compound: RTA=3.17 min; m/z (ES+)=364.2 [M+H]+.

Provenance & Evidence