Ethyl Acetate → HCID 11660311, Verbindung

HRID 1820138

Reaktionsgleichung

Reaktionsgleichung von HRID 1820138
[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.[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[C:23]=1[NH2:35].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:35][C:23]1[C:24]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:25][C:26]([F:28])=[CH:27][C:22]=1[F:21])=[O:11]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 79139Norborn-2-ylacetic acidHCID 81531DiisopropylethylamineHCID 672646582,4-Difluoro-6-morpholin-4-yl-phenylamine

Produkt 1

HCID 11660311HCID 11660311, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Bicyclo[2.2.1]hept-2-yl-acetic acid (0.20 mL), N,N-diisopropyl-ethylamine (0.50 mL) and N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N-methyl-methanaminium hexafluoro-phosphate N-oxide (0.55 g) were mixed in dry N,N-dimethylformamide (3 mL) and stirred under argon for 2 minutes. 2,4-Difluoro-6-morpholin-4-yl-phenylamine (0.20 g) dissolved in dry N,N-dimethylformamide (2 mL) was added to the reaction mixture, which was stirred at 60° 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 0.17 g (51% yield) of the title compound as a white solid. LC-MS (m/z) 351 (MH+); tR=2.94, (UV, ELSD) 96%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.12 (m, 4H), 1.41 (m, 4H), 1.87 (m, 1H), 1.99 (d, 2H), 2.13 (dd, 1H), 2.20 (m, 1H), 2.27 (dd, 1H), 2.88 (t, 4H), 3.70 (t, 4H), 6.72 (m, 1H), 6.89 (dt, 1H), 9.10 (s, 1H).

Aufarbeitung

  1. additionwas added to the reaction mixture, which
  2. stirringwas stirred at 60° 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-37b77e443dd84263b296d96cf9db4ba0
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601870B2

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