Dabco → Methyl-phenyl-carbamic Acid 5-(4-trifluoromethyl-benzoylamino)-pyridin-2-yl Ester

HRID 1179944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1179944
[OH:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH3:21][N:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:23](Cl)=[O:24].N12CCN(CC1)CC2>CN(C)C=O>[F:18][C:16]([F:19])([F:17])[C:13]1[CH:12]=[CH:11][C:10]([C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([O:1][C:23](=[O:24])[N:22]([CH3:21])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:7][CH:6]=2)=[O:20])=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178522253HCID 178522253, Verbindung

Produkt 1

HCID 69518161Methyl-phenyl-carbamic Acid 5-(4-trifluoromethyl-benzoylamino)-pyridin-2-yl EsterAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-(6-hydroxy-pyridin-3-yl)-4-trifluoromethyl-benzamide (1.41 g, 5.00 mmol), N-methyl-N-phenylcarbamoyl chloride (0.85 g, 5.00 mmol) and 1,4-diazabicyclo[2,2,2]octane (0.56 g, 5.00 mmol) in dimethylformamide (10 mL) was stirred at room temperature overnight. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50) yielding the title compound (1.34 g, 64% yield) as a white solid.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-1d05b5133cc945ae9d66626ca6bca5dd
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279470B2

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