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1-Hydroxybenzotriazole → (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-N-[2-oxo-3-(3,4,5-trifluorophenyl)piperidin-1-yl]acrylamide

HRID 546739
Notes
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Reaction equation

HRID 546739 reaction equation
C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[CH3:20][O:21][C:22]1[N:27]=[C:26](/[CH:28]=[CH:29]/[C:30]([OH:32])=O)[CH:25]=[CH:24][C:23]=1[N:33]1[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]1.[NH2:39][N:40]1[CH2:45][CH2:44][CH2:43][CH:42]([C:46]2[CH:51]=[C:50]([F:52])[C:49]([F:53])=[C:48]([F:54])[CH:47]=2)[C:41]1=[O:55]>CN(C=O)C.C(OCC)(=O)C.O.C(Cl)CCl>[CH3:20][O:21][C:22]1[N:27]=[C:26](/[CH:28]=[CH:29]/[C:30]([NH:39][N:40]2[CH2:45][CH2:44][CH2:43][CH:42]([C:46]3[CH:47]=[C:48]([F:54])[C:49]([F:53])=[C:50]([F:52])[CH:51]=3)[C:41]2=[O:55])=[O:32])[CH:25]=[CH:24][C:23]=1[N:33]1[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66633906(E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylic acidHCID 668393801-Amino-3-(3,4,5-trifluorophenyl)piperidin-2-one

Product 1

HCID 66839407(E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-N-[2-oxo-3-(3,4,5-trifluorophenyl)piperidin-1-yl]acrylamide
Yield 90.4%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDC (667 mg), HOBT (470 mg) and IPEA (1.01 mL) were added to a suspension of (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylic acid (300 mg) and 1-amino-3-(3,4,5-trifluorophenyl)piperidin-2-one (368 mg) in DMF (10 mL). The reaction solution was stirred at room temperature for 15 hours. Then, water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate-methanol system) to obtain 508 mg of the title compound. The property value of the compound is as follows.

Workup

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

Sources & evidence

ORD record
ord-a82882278a2541cc9bcfdbe2574dcf9d
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