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Benzeneacetic acid, 4-bromo- → HCID 66839577, compound

HRID 546772
Notes
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Reaction equation

HRID 546772 reaction equation
C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([OH:30])=O)=[CH:23][CH:22]=1.Cl[CH2:32][CH2:33][CH2:34]/[C:35](=[CH:40]\[C:41]1[CH:46]=[CH:45][C:44]([N:47]2[CH:51]=[C:50]([CH3:52])[N:49]=[CH:48]2)=[C:43]([O:53][CH3:54])[CH:42]=1)/[C:36]([NH:38][NH2:39])=[O:37].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(Cl)CCl>[Br:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27][C:28]([NH:39][N:38]2[CH2:32][CH2:33][CH2:34]/[C:35](=[CH:40]\[C:41]3[CH:46]=[CH:45][C:44]([N:47]4[CH:51]=[C:50]([CH3:52])[N:49]=[CH:48]4)=[C:43]([O:53][CH3:54])[CH:42]=3)/[C:36]2=[O:37])=[O:30])=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 74654Benzeneacetic acid, 4-bromo-HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 66839551HCID 66839551, compound

Product 1

HCID 66839577HCID 66839577, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

EDC (109 mg), HOBT (76.9 mg) and IPEA (408 μL) were added to a mixture of 4-bromophenylacetic acid (102 mg), 5-chloro-2-[1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene]-pentanoic acid hydrazide (200 mg) and DMF (4 mL), and the reaction solution was stirred at room temperature for 14 hours. The reaction solution was heated to 80° C. and stirred for two hours. The reaction solution was brought to room temperature. A saturated sodium bicarbonate solution was added, followed by separatory extraction with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=1:1→ethyl acetate→ethyl acetate:methanol=8:1) to obtain the title compound (111 mg). The property value of the compound is as follows.

Workup

  1. temperatureThe reaction solution was heated to 80° C.
  2. stirringstirred for two hours
  3. customwas brought to room temperature
  4. extractionfollowed by separatory extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=1:1→ethyl acetate→ethyl acetate:methanol=8:1)

Sources & evidence

ORD record
ord-142d0853d65c4017ae2f27ef242eda75
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935815B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes