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2-(4-Fluorophenyl)acetic acid → (4-fluorophenyl)acetic acid N'-{5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}pentanoyl}hydrazide

HRID 599601
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 599601
C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.Cl.[Cl:22][CH2:23][CH2:24][CH2:25]/[C:26](=[CH:31]\[C:32]1[CH:37]=[CH:36][C:35]([N:38]2[CH:42]=[C:41]([CH3:43])[N:40]=[CH:39]2)=[C:34]([O:44][CH3:45])[CH:33]=1)/[C:27]([NH:29][NH2:30])=[O:28].[F:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][C:54]([OH:56])=[O:55])=[CH:49][CH:48]=1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[F:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][C:54]([NH:30][N:29]2[CH2:23][CH2:24][CH2:25]/[C:26](=[CH:31]\[C:32]3[CH:37]=[CH:36][C:35]([N:38]4[CH:42]=[C:41]([CH3:43])[N:40]=[CH:39]4)=[C:34]([O:44][CH3:45])[CH:33]=3)/[C:27]2=[O:28])=[O:55])=[CH:49][CH:48]=1.[Cl:22][CH2:23][CH2:24][CH2:25]/[C:26](=[CH:31]\[C:32]1[CH:37]=[CH:36][C:35]([N:38]2[CH:42]=[C:41]([CH3:43])[N:40]=[CH:39]2)=[C:34]([O:44][CH3:45])[CH:33]=1)/[C:27]([NH:29][NH:30][C:54](=[O:56])[CH2:53][C:50]1[CH:49]=[CH:48][C:47]([F:46])=[CH:52][CH:51]=1)=[O:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 5

HCID 98372-(4-Fluorophenyl)acetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 670671995-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}valeric acid hydrazide dihydrochlorideHCID 86585896Sodium bicarbonate water

Produkt 2

HCID 67067381
(4-fluorophenyl)acetic acid N'-{5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}pentanoyl}hydrazide
HCID 670674402-(4-fluorophenyl)-N-{3-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}-2-oxopiperidin-1-yl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

IPEA (0.5 mL), HOBT (128 mg) and EDC (182 mg) were added to a solution of 5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}valeric acid hydrazide dihydrochloride (200 mg) and 4-fluorophenylacetic acid (73 mg) in DMF (3 mL), and the reaction solution was stirred at room temperature for six 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 75 mg of 2-(4-fluorophenyl)-N-{3-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}-2-oxopiperidin-1-yl}acetamide and 217 mg of (4-fluorophenyl)acetic acid N′-{5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}pentanoyl}hydrazide.

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-12c605a217c949adb8fdf08febf10d52
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897632B2

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