Reacción #57184

Ecuación de reacción

N′-(4-{4-(2-{3-[(dimethylamino)methyl]phenyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-[2-(methylamino)ethyl]-1H-pyrazol-3-yl}phenyl)-N,N-dimethylurea

NaOH

CH2O

water

→

title compound

Rendimiento 30.0%

N′-{4-[1-[2-(dimethylamino)ethyl]-4-(2-{3-[(dimethylamino)methyl]phenyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-N,N-dimethylurea

Rendimiento 30.0%

Disolventes

Pd(OH)2/C

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was evaporated to dryness under vacuum
2. 2
   workup.ADDITIONtreated with excess methyl isatoic anhydride polystyrene resin (˜500 mg, >1.8 mMol/g)
3. 3
   workup.STIRRINGAfter stirring at RT for 4 h the reaction
4. 4
   Filtraciónwas filtered
5. 5
   Lavadorinsed with (9:1) CHCl3/iPrOH
6. 6
   Concentraciónthe filtrate concentrated to dryness under vacuum
7. 7
   OtroPurification by Gilson HPLC

Procedimiento

To N′-(4-{4-(2-{3-[(dimethylamino)methyl]phenyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-[2-(methylamino)ethyl]-1H-pyrazol-3-yl}phenyl)-N,N-dimethylurea.3TFA (300 mg, 0.34 mMol) in MeOH (10 mL) was added with stirring at RT aq. 1 N NaOH (1.1 mL, 1.1 mMol), 37 wt. % CH2O in water (50 uL, 0.67 mMol) and 20% Pd(OH)2/C (Pearlman's catalyst) (˜10 mg). A balloon of H2 was attached and the reaction stirred at RT for 3 days. The reaction was evaporated to dryness under vacuum, taken up in (9:1) CHCl3/iPrOH (15 mL) and treated with excess methyl isatoic anhydride polystyrene resin (˜500 mg, >1.8 mMol/g). After stirring at RT for 4 h the reaction was filtered, rinsed with (9:1) CHCl3/iPrOH, and the filtrate concentrated to dryness under vacuum. Purification by Gilson HPLC provided the title compound (56.6 mg, 30%) as a white solid. ESMS [M+H]+: 551.6

Fuente