1-Hydroxybenzotriazole → (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-[2-oxo-3-(3,4,5-trifluorophenyl)piperidin-1-yl]acrylamide

HRID 2235709Notes

Reaction equation

HRID 2235709 reaction equation
C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH:24]([C:28]2[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[CH:29]=2)[C:23]1=[O:37].[CH3:38][O:39][C:40]1[CH:41]=[C:42](/[CH:52]=[CH:53]/[C:54](O)=[O:55])[CH:43]=[CH:44][C:45]=1[N:46]1[CH:50]=[C:49]([CH3:51])[N:48]=[CH:47]1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[CH3:38][O:39][C:40]1[CH:41]=[C:42](/[CH:52]=[CH:53]/[C:54]([NH:21][N:22]2[CH2:27][CH2:26][CH2:25][CH:24]([C:28]3[CH:29]=[C:30]([F:36])[C:31]([F:35])=[C:32]([F:34])[CH:33]=3)[C:23]2=[O:37])=[O:55])[CH:43]=[CH:44][C:45]=1[N:46]1[CH:50]=[C:49]([CH3:51])[N:48]=[CH:47]1

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 668393791-Amino-3-(3,4,5-trifluorophenyl)piperidin-2-one hydrochlorideHCID 86585896Sodium bicarbonate water

Product 1

HCID 66839333(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-[2-oxo-3-(3,4,5-trifluorophenyl)piperidin-1-yl]acrylamideYield 50.6%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (0.41 mL), HOBT (105 mg) and EDC (149 mg) were added to a solution of 1-amino-3-(3,4,5-trifluorophenyl)piperidin-2-one hydrochloride (109 mg) and (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (100 mg) in DMF (2 mL), and the reaction solution was stirred at room temperature for three 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 95 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 (elution solvent: ethyl acetate->ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-bad3c3eb8daa4b4ab82566be194204fa
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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