Pyrrolidine → 2-(3-Ethylureido)-5-(trifluoromethyl)benzoic acid

HRID 1171461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171461
[CH2:1]([NH:3][C:4](=[O:22])[NH:5][C:6]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:7]=1[C:8]([O:10]CC=C)=[O:9])[CH3:2].N1CCCC1>C(#N)C>[CH2:1]([NH:3][C:4](=[O:22])[NH:5][C:6]1[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:14][C:7]=1[C:8]([OH:10])=[O:9])[CH3:2]

Komponenten

4

Edukt 2

HCID 31268PyrrolidineHCID 21075131Allyl 2-(3-ethylureido)-5-(trifluoromethyl)benzoate

Produkt 1

HCID 222687522-(3-Ethylureido)-5-(trifluoromethyl)benzoic acidAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The allyl 2-(3-ethylureido)-5-(trifluoromethyl)benzoate (1.8 g, ca. 5.7 mmol) was dissolved in acetonitrile (50 mL) The solution was charged with pyrrolidine (1.0 mL, 12 mmol) and Ph(PPh3)4 (140 mg, 0.17 mmol) and then stirred for 2 h at RT before being concentrated in vacuo. The residue was diluted with EtOAc and this was washed successively with 1N HCl (2×) and brine (1×) before being dried (Na2SO4), filtered, and concentrated in vacuo. The residue was triturated with methylene chloride to afford pure 2-(3-ethylureido)-5-(trifluoromethyl)benzoic acid (0.89 g). 1H-NMR (300 MHz, d4-MeOH): δ 8.59 (d, 1H, J=9.6 Hz), 8.26 (d, 1H, J=1.5 Hz), 7.72 (dd, 1H, J=9.2, 1.8 Hz), 3.23 (q, 2H, J=7.3 Hz), 1.17 (t, 3H, J=7.2 Hz).

Aufarbeitung

  1. concentrationbefore being concentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washthis was washed successively with 1N HCl (2×) and brine (1×)
  4. dry with materialbefore being dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-340403ba5f41454093c44107cd8e17d6
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829571B2

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