1-Hydroxybenzotriazole → (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-[2-oxo-3-(3,4,5-trifluorophenyl)piperidin-1-yl]acrylamide

HRID 2235709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2235709
C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH:24]([C:28]2[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[CH:29]=2)[C:23]1=[O:37].[CH3:38][O:39][C:40]1[CH:41]=[C:42](/[CH:52]=[CH:53]/[C:54](O)=[O:55])[CH:43]=[CH:44][C:45]=1[N:46]1[CH:50]=[C:49]([CH3:51])[N:48]=[CH:47]1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[CH3:38][O:39][C:40]1[CH:41]=[C:42](/[CH:52]=[CH:53]/[C:54]([NH:21][N:22]2[CH2:27][CH2:26][CH2:25][CH:24]([C:28]3[CH:29]=[C:30]([F:36])[C:31]([F:35])=[C:32]([F:34])[CH:33]=3)[C:23]2=[O:37])=[O:55])[CH:43]=[CH:44][C:45]=1[N:46]1[CH:50]=[C:49]([CH3:51])[N:48]=[CH:47]1

Komponenten

9

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 668393791-Amino-3-(3,4,5-trifluorophenyl)piperidin-2-one hydrochlorideHCID 86585896Sodium bicarbonate water

Produkt 1

HCID 66839333(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-[2-oxo-3-(3,4,5-trifluorophenyl)piperidin-1-yl]acrylamideAusbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

IPEA (0.41 mL), HOBT (105 mg) and EDC (149 mg) were added to a solution of 1-amino-3-(3,4,5-trifluorophenyl)piperidin-2-one hydrochloride (109 mg) and (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (100 mg) in DMF (2 mL), and the reaction solution was stirred at room temperature for three hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate->ethyl acetate:methanol=5:1) to obtain 95 mg of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate->ethyl acetate:methanol=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-bad3c3eb8daa4b4ab82566be194204fa
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713993B2

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