Water → N-(4-benzoyl-pyridin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-isobutyramide

HRID 1358599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1358599
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(C(C)C)C(C)C)C.[F:25][C:26]([F:44])([F:43])[C:27]1[CH:28]=[C:29]([C:37]([CH3:42])([CH3:41])[C:38](Cl)=[O:39])[CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1.O>ClCCl>[C:8]([C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:1][C:38](=[O:39])[C:37]([C:29]1[CH:28]=[C:27]([C:26]([F:25])([F:43])[F:44])[CH:32]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:30]=1)([CH3:42])[CH3:41])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 11820052(3-Aminopyridin-4-yl)(phenyl)methanone

Produkt 1

HCID 18185386N-(4-benzoyl-pyridin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-isobutyramideAusbeute 24,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 397 mg (2 mmol) 3-amino-4-benzoylpyridine and 517 mg (4 mmol) N-ethyldiisopropylamine in 8 ml dichloromethane was cooled in an ice bath and a solution of 765 mg (2.4 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride in 8 ml dichloromethane was added dropwise. The reaction mixture was warmed to room temperature and was stirred overnight. Water (5 ml) was added and the organic layer was separated. The aqueous phase was extracted with dichloromethane. The combined organic layers were dried (magnesium sulfate) and evaporated. The residue was purified by flash chromatography to give 235 mg (24%) of the title compound as orange oil.

Aufarbeitung

  1. customthe organic layer was separated
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. customevaporated
  5. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b5e488eb699c4922baa50e83cc74e537
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596773B2

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