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Ethyl Acetate → 2-Bicyclo[2.2.1]hept-2-yl-N-(2-methyl-4-morpholin-4-yl-6-trifluoromethyl-phenyl)-acetamide

HRID 905593
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 905593
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([OH:11])=O.C(N(CC)C(C)C)(C)C.[CH3:21][C:22]1[CH:27]=[C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:25]=[C:24]([C:34]([F:37])([F:36])[F:35])[C:23]=1[NH2:38].C(OCC)(=O)C>CN(C)C=O>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([NH:38][C:23]1[C:24]([C:34]([F:35])([F:36])[F:37])=[CH:25][C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:27][C:22]=1[CH3:21])=[O:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 79139Norborn-2-ylacetic acidHCID 81531DiisopropylethylamineHCID 67406600Benzenamine, 2-methyl-4-(4-morpholinyl)-6-(trifluoromethyl)-

Produkt 1

HCID 116612162-Bicyclo[2.2.1]hept-2-yl-N-(2-methyl-4-morpholin-4-yl-6-trifluoromethyl-phenyl)-acetamideAusbeute 6 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Bicyclo[2.2.1]hept-2-yl-acetic acid (160 mg), N,N-diisopropyl-ethylamine (0.44 mL) and N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N-methyl-methanaminium hexafluoro-phosphate N-oxide (0.47 g) were mixed in dry N,N-dimethylformamide (3 mL) and stirred under argon for 2 minutes. 2-Methyl-4-morpholin-4-yl-6-trifluoromethyl-phenylamine (0.18 g) dissolved in dry N,N-dimethylformamide (2 mL) was added to the reaction mixture, which was stirred at 25° C. under argon for 16 hours. Ethyl acetate (20 mL) was added and the organic phase was washed with saturated aqueous ammonium chloride/water (1:1, 20 mL), water (20 mL), brine/water (1:1, 20 mL), dried over magnesium sulfate, concentrated in vacuo and purified by flash chromatography to furnish 16 mg (6% yield) of the title compound as a white solid. LC-MS (m/z) 397 (MH+); tR=3.12, (UV, ELSD) 91%, 98%.

Aufarbeitung

  1. additionwas added to the reaction mixture, which
  2. stirringwas stirred at 25° C. under argon for 16 hours
  3. washthe organic phase was washed with saturated aqueous ammonium chloride/water (1:1, 20 mL), water (20 mL), brine/water (1:1, 20 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c37c53cd227a428fb856985f902a1658
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08012962B2

Notizen zur Reaktion

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