Reaktion #48780

Reaktionsgleichung

DIPEA

tert-butyl 3-amino-1H-pyrazole-1-carboxylate

HATU

3-{(1S)-2-methoxy-(1-methylethyl)oxy}-5-{[4-(methylsulfonyl)phenyl]oxy}benzoic acid

→

title compound

Ausbeute 43.0%

tert-Butyl 3-({3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

Ausbeute 43.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in saturated aqueous sodium hydrogencarbonate (30 mL)
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with saturated aqueous ammonium chloride (30 mL)
5. 5
   Trocknenthen dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigePurification by column chromatography
9. 9
   Wascheneluting with 50% ethyl acetate in hexanes

Vorschrift

HATU (375 mg, 1.17 mmol) was added to 3-{(1S)-2-methoxy-(1-methylethyl)oxy}-5-{[4-(methylsulfonyl)phenyl]oxy}benzoic acid (300 mg, 0.79 mmol) followed by addition of DMF (5 mL), DIPEA (0.35 mL) and tert-butyl 3-amino-1H-pyrazole-1-carboxylate (155 mg, 0.85 mmol) and the reaction was stirred under argon for 4 h. The solvent was evaporated and the residue was dissolved in saturated aqueous sodium hydrogencarbonate (30 mL) and ethyl acetate (50 mL). The organic layer was separated, washed with saturated aqueous ammonium chloride (30 mL) then dried (MgSO4), filtered and evaporated. Purification by column chromatography, eluting with 50% ethyl acetate in hexanes, afforded the title compound as a colourless oil (185 mg, 43%).

Quelle