Реакция #992702

Уравнение реакции

sodium acetate

hydroxylamine hydrochloride

1-(3-chloro-2-pyridinyl)-N-[2-[(diethylamino)oxoacetyl]-4,6-dimethylphenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

title product

1-(3-chloro-2-pyridinyl)-N-[2-[(diethylamino)oxoacetyl]-4,6-dimethylphenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

→

title product

1-(3-chloro-2-pyridinyl)-N-[2-[(1Z)-2-(diethylamino)-1-(hydroxyimino)-2-oxoethyl]-4,6-dimethylphenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

Растворители

ethanol

water

water

ethanol

Условия реакции

Обработка

1. 1
   ТемператураThe resulting mixture was heated
2. 2
   Температураat reflux for 3 days
3. 3
   Концентрированиеconcentrated onto silica gel (0.5 g)
4. 4
   ДругоеThe residue was purified by flash chromatography on silica gel
5. 5
   Промывкаeluted with 35% ethyl acetate in hexanes

Методика

A solution of hydroxylamine hydrochloride (50 mg, 0.71 mmol) in water (0.5 mL) was added to a solution of 1-(3-chloro-2-pyridinyl)-N-[2-[(diethylamino)oxoacetyl]-4,6-dimethylphenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide (i.e. the title product of Example 2, 124 mg, 0.24 mmol) in ethanol (5 mL) at 25° C. The resulting mixture was treated with a solution of sodium acetate (200 mg) in water (2 mL). The resulting mixture was heated at reflux for 3 days and then cooled to 25° C., diluted with ethanol (30 mL) and concentrated onto silica gel (0.5 g). The residue was purified by flash chromatography on silica gel eluted with 35% ethyl acetate in hexanes to give 50 mg of the title product, a compound of the present invention, as a yellow glassy solid.

Источник