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Diisopropylethylamine → 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(2-chloro-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide

HRID 1017442
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1017442
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH:14][CH3:15].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.C(=O)(O)[O-].[Na+]>ClCCl>[F:34][C:33]([F:35])([F:36])[C:31]1[CH:30]=[C:29]([C:37]([CH3:41])([CH3:42])[C:38]([N:14]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:8]=2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH3:15])=[O:39])[CH:28]=[C:27]([C:26]([F:43])([F:25])[F:44])[CH:32]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 18403335[4-(2-Chloro-phenyl)-pyridin-3-yl]-methyl-amine

Produkt 1

HCID 99151582-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(2-chloro-phenyl)-pyridin-3-yl]-N-methyl-isobutyramideAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
37.5 °C

Versuchsvorschrift

A solution of 12.2 g (55.8 mmol) [4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-amine and 15.3 ml (89 mmol) N-ethyldiisopropylamine in 130 ml dichloromethane was cooled in an ice bath and a solution of 19 g (59.6 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride in 30 ml dichloromethane was added dropwise. The reaction mixture was warmed to 35-40° C. for 20 h, cooled to room temperature again and was stirred with 250 ml saturated sodium bicarbonate solution. The organic layer was separated and 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 24.7 g (88%) of the title compound as white crystals.

Aufarbeitung

  1. temperaturecooled to room temperature again
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried (magnesium sulfate)
  5. customevaporated
  6. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-04207562b0444329b69aa55e3cc7e459
Quelldatensatz
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06479483B2

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