Potassium Iodide → HCID 11577086, compound

Participants

Reaction Steps

To a solution of (R)-3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-(5-thiocyanato-thiazol-2-yl)-propionamide (200 mg, 0.46 mmol) in methanol (2.5 mL) and DCM (2.5 mL) was added dithiothreitol (71 mg, 0.46 mmol), and the mixture was stirred at room temperature for 1 h. 2-Chloroethyl-diethylamine (158 mg, 0.92 mmol), potassium carbonate (235 mg, 0.46 mmol), and potassium iodide (10 mg) were added and the reaction mixture was stirred for another 3 h at room temperature. Water (5 mL) and DCM (10 mL) were added and the organic phase was isolated and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo, and the residue was purified on a silica gel column (isocratic from 100% DMC to 100% ethyl acetate with 1% TEA) to give colourless crystals of (R)-3-cyclopentyl-N-[5-(2-diethylamino-ethylsulfanyl)-thiazol-2-yl]-2-(4-methanesulfonyl-phenyl)-propionamide. Yield: 150 mg (64%). 1H-NMR (CDCl3): δ 11.50 (broad s, 1H), 7.86 (d, 2H), 7.51 (d, 2H), 7.48 (s, 1H), 3.76 (t, 1H), 3.04 (s, 3H), 2.86 (t, 2H), 2.71 (t, 2H), 2.54 (q, 4H), 2.26 (m, 1H), 1.90 (m, 1H), 1.79-1.43 (m, 8H), 1.12 (m, 1H), 1.00 (t, 6H); HPLC-MS: m/z=510 (M+1).

Provenance & Evidence