Pentanoic Acid → Pentanoic acid(2,6-dimethyl-4-morpholin-4-yl-phenyl)-amide

HRID 2068853

Reaktionsgleichung

Reaktionsgleichung von HRID 2068853
[C:1]([OH:7])(=O)[CH2:2][CH2:3][CH2:4][CH3:5].C(N(CC)C(C)C)(C)C.[CH3:17][C:18]1[CH:23]=[C:22]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:21]=[C:20]([CH3:30])[C:19]=1[NH2:31].C(OCC)(=O)C>CN(C)C=O>[CH3:17][C:18]1[CH:23]=[C:22]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:21]=[C:20]([CH3:30])[C:19]=1[NH:31][C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

6

Edukt 4

HCID 7991Pentanoic AcidHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 230094142,6-Dimethyl-4-morpholin-4-yl-phenylamine

Produkt 1

HCID 11630683Pentanoic acid(2,6-dimethyl-4-morpholin-4-yl-phenyl)-amideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Pentanoic acid (0.37 g), N,N-diisopropyl-ethylamine (1.51 mL) and N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N-methyl-methanaminium hexafluoro-phosphate N-oxide (1.66 g) were mixed in dry N,N-dimethylformamide (3 mL) and stirred under argon for 2 minutes. 2,6-Dimethyl-4-morpholin-4-yl-phenylamine (0.50 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 0.28 g (40% yield) of the title compound as a white solid. LC-MS (m/z) 291 (MH+); tR=1.61, (UV, ELSD) 99%, 99%. 1H NMR (500 MHz, DMSO-d6): 0.91 (t, 3H), 1.34 (m, 2H), 1.58 (qui, 2H), 2.06 (s, 6H), 2.27 (t, 2H), 3.04 (t, 4H), 3.71 (t, 4H), 6.62 (s, 2H), 8.94 (s, 1H).

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-cfcee4776993470d8fee5e6eb1fa9b42
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299075B2

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