Diisopropylethylamine → 5-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N'-{(Z)-2-fluoro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide

HRID 546672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546672
C(N(C(C)C)CC)(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.Cl.[Cl:26][CH2:27][CH2:28][CH2:29][CH:30]([C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[C:37]([F:43])[CH:36]=1)[C:31]([NH:33][NH2:34])=[O:32].[F:44]/[C:45](=[CH:49]\[C:50]1[CH:55]=[CH:54][C:53]([N:56]2[CH:60]=[C:59]([CH3:61])[N:58]=[CH:57]2)=[C:52]([O:62][CH3:63])[CH:51]=1)/[C:46](O)=[O:47].O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[F:44]/[C:45](=[CH:49]\[C:50]1[CH:55]=[CH:54][C:53]([N:56]2[CH:60]=[C:59]([CH3:61])[N:58]=[CH:57]2)=[C:52]([O:62][CH3:63])[CH:51]=1)/[C:46]([NH:34][NH:33][C:31](=[O:32])[CH:30]([C:35]1[CH:36]=[C:37]([F:43])[C:38]([F:42])=[C:39]([F:41])[CH:40]=1)[CH2:29][CH2:28][CH2:27][Cl:26])=[O:47]

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 66838904(Z)-2-fluoro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acidHCID 668392315-Chloro-2-(3,4,5-trifluorophenyl)pentanoic acid hydrazide hydrochlorideHCID 86585896Sodium bicarbonate water

Produkt 1

HCID 668388825-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N'-{(Z)-2-fluoro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

IPEA (0.14 mL) and BOPCl (100 mg) were added to a solution of 5-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid hydrazide hydrochloride (83 mg) and (Z)-2-fluoro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (CAS No. 870838-71-4, 72 mg) in methylene chloride (5 mL), and the reaction solution was stirred at room temperature for 13 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: heptane:ethyl acetate=1:1→ethyl acetate→ethyl acetate:methanol=9:1) to obtain 84 mg of the title compound. The property value of the compound is 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: heptane:ethyl acetate=1:1→ethyl acetate→ethyl acetate:methanol=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-e60f0495c0c34e29884afc9df11f4ddc
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935815B2

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