Water → (2E)-N-[3-(2-Bromo-4-fluorophenyl)-2-oxo-1-piperidinyl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-propenamide

HRID 1009458Notes

Reaction equation

HRID 1009458 reaction equation
C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[CH3:16][O:17][C:18]1[CH:19]=[C:20](/[CH:30]=[CH:31]/[C:32]([OH:34])=O)[CH:21]=[CH:22][C:23]=1[N:24]1[CH:28]=[C:27]([CH3:29])[N:26]=[CH:25]1.[NH2:35][N:36]1[CH2:41][CH2:40][CH2:39][CH:38]([C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=2[Br:49])[C:37]1=[O:50].O>CN(C=O)C.C(OCC)(=O)C>[Br:49][C:43]1[CH:44]=[C:45]([F:48])[CH:46]=[CH:47][C:42]=1[CH:38]1[CH2:39][CH2:40][CH2:41][N:36]([NH:35][C:32](=[O:34])/[CH:31]=[CH:30]/[C:20]2[CH:21]=[CH:22][C:23]([N:24]3[CH:28]=[C:27]([CH3:29])[N:26]=[CH:25]3)=[C:18]([O:17][CH3:16])[CH:19]=2)[C:37]1=[O:50]

Participants

7

Reactant 4

HCID 962WaterHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 66839548HCID 66839548, compound

Product 1

HCID 66839421(2E)-N-[3-(2-Bromo-4-fluorophenyl)-2-oxo-1-piperidinyl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-propenamideYield 46.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

BOPCl (1.48 g) was added to a suspension of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (1.0 g), 1-amino-3-(2-bromo-4-fluorophenyl)piperidin-2-one (1.15 g) and TEA (1.1 mL) in DMF (20 mL), and the reaction solution was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. The resulting organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate-methanol system) to obtain 953 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-0a0605478a664fe282ff70272913a167
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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