Lawesson's reagent → HCID 60148823, compound

Participants

Reaction Steps

3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carbohydrazide (85 mg, 0.2 mmol) was treated with formic acid (6.4 μL, 0.2 mmol). The mixture was stirred at r.t. for 72 h. To the reaction mixture was added water, the resulting precipitate was collected, washed with water and dried in vacuum to give 61 mg of the intermediate as a colorless solid. To a solution of the intermediate 3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(tri fluoromethyl)-1H-pyrazol-4-yl)-N′-formyl isoxazole-4-carbohydrazide (20 mg, 0.038 mmol) in dioxane (2 mL) was added Lawesson's Reagent (0.033 mL, 0.1 mmol). The mixture was stirred at reflux for 3 h. The mixture was diluted with dichloromethane and washed with water (3×), dried over sodium sulfate, filtered and concentrated under reduced pressure. The product was purified by pTLC (EE/PE 1:1) to give 6 mg of example IB-8 as a colorless solid (yield 31%). Result of LC/MS MH+: 525.72; 1H NMR (MeOD): δ 7.35 (t, 1H), 7.49 (d, 1H), 7.59-7.71 (m, 5H), 8.37 (s, 1H), 9.38 (s, 1H)

Provenance & Evidence