P-Anisidine → HCID 58842857, Verbindung

HRID 16958

Reaktionsgleichung

Reaktionsgleichung von HRID 16958
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C1N=CN([C:15](N2C=NC=C2)=[O:16])C=1.[CH2:22]([O:24][C:25](=[O:44])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N:34]2[C:38]([NH2:39])=[CH:37][C:36]([C:40]([CH3:43])([CH3:42])[CH3:41])=[N:35]2)[CH:29]=1)[CH3:23]>CN(C=O)C>[CH2:22]([O:24][C:25](=[O:44])[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N:34]2[C:38]([NH:39][C:15]([NH:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[O:16])=[CH:37][C:36]([C:40]([CH3:43])([CH3:42])[CH3:41])=[N:35]2)[CH:29]=1)[CH3:23]

Komponenten

5

Edukt 3

HCID 7732P-AnisidineHCID 682631,1'-CarbonyldiimidazoleHCID 58842892ethyl 3-(3-(3-t-butyl-5-amino-1H-pyrazol-1-yl)phenyl)propanoate

Produkt 1

HCID 58842857HCID 58842857, VerbindungAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A mixture of 4-methoxy-phenylamine (123 mg, 1.0 mmol) and CDI (165 mg, 1.0 mmol) in DMF (2 mL) was stirred at RT for 30 min, and was then added a solution of Example Z (315 mg, 1.0 mmol) in DMF (2 mL). The resulting mixture was stirred at RT overnight then quenched with of water (50 mL). The reaction mixture was extracted with ethyl acetate (3×50 mL) and the combined organic extracts were washed with brine, dried (NaSO4), filtered, concentrated under reduced presume to yield a residue which was purified by flash chromatography to afford 3-(3-{3-t-butyl-5-[3-(4-methoxy-phenyl)-ureido]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester (210 mg, 45%). 1H-NMR (CD3OD): 7.46 (t, J=7.6 Hz, 1H), 7.38 (s, 1H), 7.34 (d, J=7.6 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H), 6.84 (d, J=8.4 Hz, 2H), 6.38 (s, 1H), 4.09 (q, J=7.2 Hz, 2H), 3.75 (s, 3H), 3.00 (t, J=7.6 Hz, 2H), 2.68 (t, J=7.6 Hz, 2H), 1.33 (s, 9H), 1.20 (t, J=7.6 Hz, 3H); MS (ESI) m/z: 465 (M+H+).

Aufarbeitung

  1. stirringThe resulting mixture was stirred at RT overnight
  2. customthen quenched with of water (50 mL)
  3. extractionThe reaction mixture was extracted with ethyl acetate (3×50 mL)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (NaSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced presume
  8. customto yield a residue which
  9. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5fff6ba8bad6477891b99d6173706b19
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737283B2

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