2-Aminothiazole → HCID 178527553, compound

Participants

Reaction Steps

To a solution of 3-(3-chloro-benzyl)-4-methoxymethyl-5-(4-triisopropylsilanylsulfanyl-phenyl)-4H-[1,2,4]triazole (0.42 mmol) in acetonitrile (5 mL) at 0° C. was added potassium nitrate (1.05 mmol) and sulfuryl chloride, and the mixture was stirred for 1 h. The inorganic precipitate was filtered and washed with acetonitrile. The organic phase was concentrated and the residue was dissolved in THF (1.3 mL). To the solution were added thiazol-2-ylamine (0.5 mmol) and excess pyridine. The mixture was stirred over weekend. After concentration, the residue in 6N HCl (1 mL) and ethanol (1 mL) was stirred at 80° C. for 16 h before the reaction mixture was concentrated, the crude product was purified by reverse phase HPLC to give 4-[5-(3-chloro-benzyl)-4H-[1,2,4]triazol-3-yl]-N-thiazol-2-yl-benzenesulfonamide (0.1 mmol).

Provenance & Evidence