Reacción #48817

Ecuación de reacción

DIPEA

3-{(phenylmethyl)oxy}-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)benzoic acid

HATU

1-isopropyl-1H-pyrazol-3-amine

→

title compound

Rendimiento 65.0%

3-(Benzyloxy)-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(1-isopropyl-1H-pyrazol-3-yl)benzamide

Rendimiento 65.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe DMF was removed in vacuo
2. 2
   OtroThe solvent was evaporated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in 5%
4. 4
   Lavadothe organic layer was further washed with sat. aqueous sodium bicarbonate solution (30 mL) and brine (30 mL)
5. 5
   OtroThe organic layer was separated
6. 6
   Secadodried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated
9. 9
   OtroPurification by column chromatography
10. 10
    Lavadoeluting with 1:4 to 1:3 ethyl acetate

Procedimiento

DIPEA (3.11 mL, 18.03 mmol) was added to a solution of 3-{(phenylmethyl)oxy}-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)benzoic acid (3.00 g, 7.21 mmol), HATU (3.12 g, 8.21 mmol) and 1-isopropyl-1H-pyrazol-3-amine (1.13 g, 9.01 mmol) in DMF (10 mL). The resulting mixture was stirred at ambient temperature for 16 hours. The DMF was removed in vacuo. The solvent was evaporated and the residue was dissolved in 5% w/v citric acid (50 mL) and ethyl acetate (30 mL) and diethyl ether (30 mL) and the organic layer was further washed with sat. aqueous sodium bicarbonate solution (30 mL) and brine (30 mL). The organic layer was separated, then dried (MgSO4), filtered and evaporated. Purification by column chromatography, eluting with 1:4 to 1:3 ethyl acetate:hexanes, afforded the title compound as a colourless oil (2.40 g, 65%).

Fuente