Triethylamine → 2-(Quinolin-4-ylmethylthio)-N-(4-trifluoromethoxyphenyl)pyridine-3-carboxamide

HRID 599363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 599363
C(N(CC)CC)C.[SH:8][C:9]1[C:14]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1.Cl[CH2:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=[CH:33][CH:32]=1.C(OCC)(=O)C>CN(C)C=O>[N:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:31]([CH2:30][S:8][C:9]2[C:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:26])([F:27])[F:28])=[CH:20][CH:19]=3)=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:32][CH:33]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 123557014-(Chloromethyl)quinolineHCID 1785222352-mercapto-N-(4-trifluoromethoxyphenyl)pyridine-3-carboxamide

Produkt 1

HCID 118470442-(Quinolin-4-ylmethylthio)-N-(4-trifluoromethoxyphenyl)pyridine-3-carboxamideAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Triethylamine (66 μL, 0.47 mmol) was added to a solution of 2-mercapto-N-(4-trifluoromethoxyphenyl)pyridine-3-carboxamide (Reference Compound No. 8-3, 52 mg, 0.17 mmol) and 4-(chloromethyl)quinoline (Reference Compound No. 5-1, 28 mg, 0.16 mmol) in anhydrous N,N-dimethylformamide (11.0 mL) at room temperature, and the mixture was stirred for 18 hours. Ethyl acetate (50 mL) was added thereto, then the whole was washed with saturated aqueous sodium hydrogencarbonate solution (5 mL) and brine (50 mL). The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the resulting residue was purified by silica gel column chromatography to give 40 mg of the title compound as a white amorphous (Yield: 52%).

Aufarbeitung

  1. washthe whole was washed with saturated aqueous sodium hydrogencarbonate solution (5 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ce95029d13354666ae5c0ec456e1fa88
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897774B2

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