Diisopropylethylamine → (Z)-2-fluoro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-[2-oxo-3-(2,4,6-trifluorophenyl)piperidin-1-yl]acrylamide

HRID 546670Notes

Reaction equation

HRID 546670 reaction equation
C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[F:16]/[C:17](=[CH:21]\[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]2)=[C:24]([O:34][CH3:35])[CH:23]=1)/[C:18]([OH:20])=O.[NH2:36][N:37]1[CH2:42][CH2:41][CH2:40][CH:39]([C:43]2[C:48]([F:49])=[CH:47][C:46]([F:50])=[CH:45][C:44]=2[F:51])[C:38]1=[O:52].C(N(C(C)C)CC)(C)C.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[F:16]/[C:17](=[CH:21]\[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]2)=[C:24]([O:34][CH3:35])[CH:23]=1)/[C:18]([NH:36][N:37]1[CH2:42][CH2:41][CH2:40][CH:39]([C:43]2[C:44]([F:51])=[CH:45][C:46]([F:50])=[CH:47][C:48]=2[F:49])[C:38]1=[O:52])=[O:20]

Participants

8

Reactant 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 668390821-Amino-3-(2,4,6-trifluorophenyl)piperidin-2-oneHCID 86585896Sodium bicarbonate water

Product 1

HCID 66838918(Z)-2-fluoro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-[2-oxo-3-(2,4,6-trifluorophenyl)piperidin-1-yl]acrylamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

BOPCl (221 mg) was added to a suspension of (Z)-2-fluoro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (CAS No. 870838-71-4, 240 mg), 1-amino-3-(2,4,6-trifluorophenyl)piperidin-2-one (106 g) and IPEA (0.45 mL) in DMF (5 mL), and the reaction solution was stirred at room temperature for 16 hours. Saturated sodium bicarbonate water and ethyl acetate were added to the reaction mixture and the organic layer was separated. The resulting organic layer was 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) to obtain 110 mg of the title compound. The property value of the compound is 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 resulting residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate)

Sources & evidence

ORD record
ord-8d0320686fe94f9a9fac64e1d508d792
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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