Water → 5-(4-Chlorophenyl)-2-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Participants

Reaction Conditions

Reaction Steps

500 mg (1.63 mmol) of the compound from Example 5A and 449 mg (3.25 mmol) of potassium carbonate were dissolved in 4 ml of acetonitrile, and 287 mg (1.71 mmol) of 2-chloro-5-(chloromethyl)-1,3-thiazole were added. The mixture was stirred at 80° C. for 1.5 h. After cooling to RT, 10 ml of water were added and the mixture was extracted three times with in each case 10 ml of ethyl acetate. The combined organic phases were washed with 10 ml of saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:1, then 1:1). This gave 619 mg (87% of theory) of the target compound.

Provenance & Evidence