반응 #48780

반응 방정식

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

수율 43.0%

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

수율 43.0%

용매

DMF

반응 조건

후처리

1. 1
   기타The solvent was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in saturated aqueous sodium hydrogencarbonate (30 mL)
3. 3
   기타The organic layer was separated
4. 4
   세척washed with saturated aqueous ammonium chloride (30 mL)
5. 5
   건조then dried (MgSO4)
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타Purification by column chromatography
9. 9
   세척eluting with 50% ethyl acetate in hexanes

실험 절차

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%).

출처