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

HRID 2369348노트

반응식

HRID 2369348 반응식
C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.FC(F)(F)C(O)=O.[CH3:27][O:28][C:29]1[N:34]=[C:33](/[CH:35]=[CH:36]/[C:37]([OH:39])=O)[CH:32]=[CH:31][C:30]=1[N:40]1[CH:44]=[C:43]([CH3:45])[N:42]=[CH:41]1.[NH2:46][N:47]1[CH2:52][CH2:51][CH2:50][CH:49]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:59]([F:62])([F:61])[F:60])[C:48]1=[O:63].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[CH3:27][O:28][C:29]1[N:34]=[C:33](/[CH:35]=[CH:36]/[C:37]([NH:46][N:47]2[CH2:52][CH2:51][CH2:50][CH:49]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=3[C:59]([F:60])([F:61])[F:62])[C:48]2=[O:63])=[O:39])[CH:32]=[CH:31][C:30]=1[N:40]1[CH:44]=[C:43]([CH3:45])[N:42]=[CH:41]1

참가 물질

9

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 666173261-Amino-3-(2-trifluoromethylphenyl)piperidin-2-oneHCID 66633905(E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylic acid trifluoroacetate

생성물 1

HCID 66617336(E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-N-[2-oxo-3-(2-trifluoromethylphenyl)piperidin-1-yl]acrylamide수율 84.8%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

EDC (834 mg), HOBT (588 mg) and IPEA (2.03 mL) were added to a suspension of (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylic acid trifluoroacetate (1.42 g) and 1-amino-3-(2-trifluoromethylphenyl)piperidin-2-one (750 mg) in DMF (30 mL). After stirring at room temperature for 14 hours, a saturated sodium bicarbonate solution and ethyl acetate 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 (carrier: Chromatorex NH; elution solvent: ethyl acetate-methanol system) to obtain 1.23 g of the title compound. The property values of the compound are as follows.

후처리

  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 (carrier: Chromatorex NH; elution solvent: ethyl acetate-methanol system)

출처 및 근거

ORD 기록
ord-32a6ecb9b1fe42e19e3efb32845787eb
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703954B2

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