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 599601Notes

Reaction equation

HRID 599601 reaction equation
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]

Participants

10

Reactant 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

Product 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}hydrazideHCID 670674402-(4-fluorophenyl)-N-{3-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}-2-oxopiperidin-1-yl}acetamide

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-12c605a217c949adb8fdf08febf10d52
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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