cyclohexa-3,5-diene-1,2-dione

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (1S,4S)-4-isopropyl-4-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopent-2-en-1-amine (3.5 g, 9.2 mmol) and 3,5-Cyclohexadiene-1,2-dione, 3,5-bis(1,1-dimethylethyl)-(2.20 g, 9.99 mmol) in Methanol (85 mL) was stirred at room temperature for 30 minutes. Tetrahydrofuran (85 mL) and 1N HCl (10 mL) were added and the resulting mixture was stirred overnight at room temperature. The mixture was diluted with water and the organics evaporated. The remaining aqueous was made basic with 1N NaOH and extracted with EtOAc three times. The combined extracts were dried (Magnesium sulfate), filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography (1:1 EtOAc/Hexanes) to yield (3.16 g, 90%) of the title compound. MS calculated for C19H22F3N3O2: (M+H) 382; found 382.1. Step B: extracted with EtOAc three times The combined extracts were dried (Magnesium sulfate) filtered concentrated in vacuo The crude residue was purified by flash column chromatography (1:1 EtOAc/Hexanes)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (1S,4S)-4-isopropyl-4-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopent-2-en-1-amine (3.5 g, 9.2 mmol) and 3,5-Cyclohexadiene-1,2-dione, 3,5-bis(1,1-dimethylethyl)-(2.20 g, 9.99 mmol) in Methanol (85 mL) was stirred at room temperature for 30 minutes. Tetrahydrofuran (85 mL) and 1N HCl (10 mL) were added and the resulting mixture was stirred overnight at room temperature. The mixture was diluted with water and the organics evaporated. The remaining aqueous was made basic with 1N NaOH and extracted with EtOAc three times. The combined extracts were dried (Magnesium sulfate), filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography (1:1 EtOAc/Hexanes) to yield (3.16 g, 90%) of the title compound. MS calculated for C19H22F3N3O2: (M+H) 382; found 382.1. Step B: extracted with EtOAc three times The combined extracts were dried (Magnesium sulfate) filtered concentrated in vacuo The crude residue was purified by flash column chromatography (1:1 EtOAc/Hexanes)

Conditions: temp:0.00; pressure:0.00; stir: