Reacción #48870

Ecuación de reacción

DIPEA

HATU

3-(benzyloxy)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoic acid

1-Methyl-1H-pyrazole-3-amine

→

title compound

Rendimiento 78.4%

3-(Benzyloxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzamide

Rendimiento 78.4%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate (500 mL)
3. 3
   Lavadowashed with citric acid solution (200 mL), sodium hydrogen carbonate solution (150 mL), and saturated brine solution (2×150 mL)
4. 4
   OtroThe organic layer was separated
5. 5
   Secadodried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated
8. 8
   OtroPurification by column chromatography
9. 9
   Lavadoeluting with 1:4 to 1:1 ethyl acetate

Procedimiento

HATU (23.5 g, 61.8 mmol) was added to 3-(benzyloxy)-5-{(1S)-1-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzoic acid (23.6 g, 51.5 mmol), followed by addition of DMF (140 mL), and cooled to 0° C. 1-Methyl-1H-pyrazole-3-amine (6.00 g. 61.8 mmol) was added followed by DIPEA (21.3 mL) and the reaction was stirred under argon at 0° C. for 3 hours. The solvent was evaporated and the residue was dissolved in ethyl acetate (500 mL) and washed with citric acid solution (200 mL), sodium hydrogen carbonate solution (150 mL), and saturated brine solution (2×150 mL). The organic layer was separated and dried (MgSO4), filtered and evaporated. Purification by column chromatography, eluting with 1:4 to 1:1 ethyl acetate:hexanes, afforded the title compound as a colourless oil (21.7 g).

Fuente