1-Hydroxybenzotriazole → (E)-3-[5-(1H-imidazol-1-yl)-6-methoxypyridin-2-yl]-N-[2-oxo-3-(2-trifluoromethylphenyl)piperidin-1-yl]acrylamide

HRID 546789Notes

Reaction equation

HRID 546789 reaction equation
C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:36])([F:35])[F:34])[C:22]1=[O:37].[N:38]1([C:43]2[CH:44]=[CH:45][C:46](/[CH:51]=[CH:52]/[C:53](O)=[O:54])=[N:47][C:48]=2[O:49][CH3:50])[CH:42]=[CH:41][N:40]=[CH:39]1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(Cl)CCl>[N:38]1([C:43]2[CH:44]=[CH:45][C:46](/[CH:51]=[CH:52]/[C:53]([NH:20][N:21]3[CH2:26][CH2:25][CH2:24][CH:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]([F:34])([F:35])[F:36])[C:22]3=[O:37])=[O:54])=[N:47][C:48]=2[O:49][CH3:50])[CH:42]=[CH:41][N:40]=[CH:39]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 666173261-Amino-3-(2-trifluoromethylphenyl)piperidin-2-oneHCID 66839409(E)-3-[5-(1H-imidazol-1-yl)-6-methoxypyridin-2-yl]acrylic acid

Product 1

HCID 66839589(E)-3-[5-(1H-imidazol-1-yl)-6-methoxypyridin-2-yl]-N-[2-oxo-3-(2-trifluoromethylphenyl)piperidin-1-yl]acrylamideYield 130.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

IPEA (742 μL), EDC (206 mg) and HOBT (146 mg) were added to a mixture of 1-amino-3-(2-trifluoromethylphenyl)piperidin-2-one (185 mg), (E)-3-[5-(1H-imidazol-1-yl)-6-methoxypyridin-2-yl]acrylic acid (340 mg) and DMF (5 mL), and the reaction solution was stirred at room temperature for 14 hours. A saturated sodium bicarbonate solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate→ethyl acetate:methanol=9:1) to obtain the title compound (453 mg). The property value of the compound is as follows.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate→ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-231f77c77e6240b8ad966c4e0fcb90c4
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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