Reacción #57149

Ecuación de reacción

N-phenyl-N′-{4-[1-(2-propen-1-yl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}urea

acetone

water

N-methylmorpholine N-oxide

→

title compound

Rendimiento 14.0%

N-{4-[1-(2,3-dihydroxypropyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-N′-phenylurea

Rendimiento 14.0%

Disolventes

t-butanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with saturated aqueous sodium sulfate (11 mL)
2. 2
   Filtraciónfiltered through a pad of celite (rinsing with ethyl acetate)
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   OtroThe residue was purified by Gilson reverse phase HPLC

Procedimiento

To a solution of N-phenyl-N′-{4-[1-(2-propen-1-yl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}urea (0.18 mmol) in 5:1 acetone:water (1.2 mL) was added N-methylmorpholine N-oxide (0.276 mmol) followed by a 2.5% solution of osmium tetroxide in t-butanol (93.5 mg). The reaction mixture was stirred at room temperature for 18 h. The reaction was quenched with saturated aqueous sodium sulfate (11 mL), filtered through a pad of celite (rinsing with ethyl acetate) and concentrated in vacuo. The residue was purified by Gilson reverse phase HPLC to afford the title compound as a white solid (14%). ESMS [M+H]+: 469.2

Fuente