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

HRID 546789노트

반응식

HRID 546789 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-231f77c77e6240b8ad966c4e0fcb90c4
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935815B2

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