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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
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HRID 546739 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 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

생성물 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]acrylamide수율 90.4%

시약·촉매·용매 4

HCID 111,2-Dichloroethane용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a82882278a2541cc9bcfdbe2574dcf9d
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935815B2

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