Reaktion #45240

Reaktionsgleichung

4-chlorobenzoic acid

solution

3-[3-(5-amino-3-t-butyl-pyrazol-1-yl)-phenyl]-propionic acid ethyl ester

→

3-{3-[3-t-butyl-5-(4-chloro-benzoylamino)-pyrazol-1-yl]-phenyl}-propionic acid ethyl ester

Ausbeute 64.0%

Lösungsmittel

SOCl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for 2 h
2. 2
   SonstigeAfter removal of the solvent
3. 3
   workup.DISSOLUTIONthe residue was dissolved into CH2Cl2 (5 mL)
4. 4
   SonstigeAfter quenching with water (50 mL)
5. 5
   Extraktionthe reaction mixture was extracted with CH2Cl2 (3×100 mL)
6. 6
   WaschenThe combined organic extracts were washed with brine
7. 7
   Trocknendried (NaSO4)
8. 8
   Filtrationfiltered
9. 9
   EinengenAfter concentrated under reduced pressure
10. 10
    Sonstigethe residue was purified by flash chromatography

Vorschrift

A solution of 4-chlorobenzoic acid (312 mg, 2.0 mmol) in SOCl2 (10 mL) was heated to reflux for 2 h. After removal of the solvent, the residue was dissolved into CH2Cl2 (5 mL) and was dropped into a solution of Example Z (315 mg, 1.0 mmol) in CH2Cl2 (10 mL) at 0° C., was then stirred at RT overnight. After quenching with water (50 mL), the reaction mixture was extracted with CH2Cl2 (3×100 mL). The combined organic extracts were washed with brine, dried (NaSO4) and filtered. After concentrated under reduced pressure, the residue was purified by flash chromatography to afford 3-{3-[3-t-butyl-5-(4-chloro-benzoylamino)-pyrazol-1-yl]-phenyl}-propionic acid ethyl ester (290 mg, 64%). 1H-NMR (CDCL3): 8.02 (s, 1H), 7.67 (d, J=8.4 Hz, 2H), 7.46 (t, J=7.6 Hz, 1H), 7.44 (d, J=8.4 Hz, 2H), 7.36 (t, J=8.4 Hz, 3H), 6.87 (s, 1H), 4.06 (q, J=7.6 Hz, 2H), 3.02 (t, J=7.6 Hz, 2H), 2.67 (t, J=7.6 Hz, 2H), 1.40 (s, 9H), 1.12 (t, J=7.6 Hz, 3H); MS (ESI) m/z: 454 (M+H+).

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