Ethyl Acetate → HCID 24852339, compound

HRID 599545Notes

Reaction equation

HRID 599545 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30]3)=[C:25]([O:35][CH3:36])[CH:24]=2)[NH:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[O:8].C(OCC)(=O)C.O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[C:11](/[CH:21]=[CH:22]/[C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30]4)=[C:25]([O:35][CH3:36])[CH:24]=3)[N:10]3[CH2:4][CH2:5][NH:6][C:7](=[O:8])[C:9]=23)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 86585896Sodium bicarbonate waterHCID 178489891HCID 178489891, compound

Product 1

HCID 24852339HCID 24852339, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (containing mineral oil at 60%, 3 mg) was added to a solution of 5-(4-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1H-imidazole-4-carboxylic acid (2-chloroethyl)amide (15 mg) in DMF (2 mL) at room temperature, and the reaction solution was stirred at room temperature for 30 minutes. 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 (carrier: Chromatorex™ NH; elution solvent: ethyl acetate→ethyl acetate:methanol=5:1) to obtain 10 mg of the title compound. The property values of the compound are as follows.

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 (carrier: Chromatorex™ NH; elution solvent: ethyl acetate→ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-35e9c70bf73547ed810c013c3066f9ac
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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