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HCID 59253395, Verbindung → HCID 86640292, Verbindung

HRID 1258546
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Reaktionsgleichung

Reaktionsgleichung von HRID 1258546
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]#[N:19])=[C:6]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:7]=1.[CH3:20][C:21]1[CH:29]=[C:28]([C:30]([F:39])([C:35]([F:38])([F:37])[F:36])[C:31]([F:34])([F:33])[F:32])[CH:27]=[C:26]([CH3:40])[C:22]=1[C:23](Cl)=[O:24]>O1CCCC1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[C:18]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:23](=[O:24])[C:22]2[C:21]([CH3:20])=[CH:29][C:28]([C:30]([F:39])([C:31]([F:32])([F:33])[F:34])[C:35]([F:36])([F:37])[F:38])=[CH:27][C:26]=2[CH3:40])=[CH:7][C:6]=1[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)#[N:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 59253395HCID 59253395, VerbindungHCID 68526880HCID 68526880, Verbindung

Produkt 1

HCID 86640292HCID 86640292, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel
HCID 516892
Sodium Bicarbonate
Lösungsmittel

Versuchsvorschrift

To a solution of N-(5-amino-2-cyano-phenyl)-4-fluoro-benzamide (0.20 g, 0.78 mmol) (Example I9) in anhydrous tetrahydrofuran (2.5 ml) under an atmosphere of nitrogen was added at room temperature a solution of 2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-benzoyl chloride (0.332 g, 1.04 mmol) (Example I4) in anhydrous tetrahydrofuran (2.5 ml). The reaction mixture was stirred at room temperature for 48 hours. The reaction mixture was diluted with ethyl acetate and aqueous sodium hydrogen carbonate (saturated). The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1) to give N-[4-cyano-3-(4-fluoro-benzoylamino)-phenyl]-2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-benzamide (131 mg, 66% yield). 1H-NMR (CDCl3, 400 MHz): 8.98 (s, 1H), 8.51 (d, 1H), 8.45 (s, 1H), 8.33 (s, 1H), 8.21 (dd, 1H), 7.84 (m, 2H), 7.68 (d, 1H), 7.34 (s, 1H), 6.78 (t, 2H) ppm.

Aufarbeitung

  1. customwas added at room temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted twice with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-c4b1dd3ea25e4a429001081da6a1a179
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466180B2

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