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

HRID 2235709노트

반응식

HRID 2235709 반응식
C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH:24]([C:28]2[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[CH:29]=2)[C:23]1=[O:37].[CH3:38][O:39][C:40]1[CH:41]=[C:42](/[CH:52]=[CH:53]/[C:54](O)=[O:55])[CH:43]=[CH:44][C:45]=1[N:46]1[CH:50]=[C:49]([CH3:51])[N:48]=[CH:47]1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[CH3:38][O:39][C:40]1[CH:41]=[C:42](/[CH:52]=[CH:53]/[C:54]([NH:21][N:22]2[CH2:27][CH2:26][CH2:25][CH:24]([C:28]3[CH:29]=[C:30]([F:36])[C:31]([F:35])=[C:32]([F:34])[CH:33]=3)[C:23]2=[O:37])=[O:55])[CH:43]=[CH:44][C:45]=1[N:46]1[CH:50]=[C:49]([CH3:51])[N:48]=[CH:47]1

참가 물질

9

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 668393791-Amino-3-(3,4,5-trifluorophenyl)piperidin-2-one hydrochlorideHCID 86585896Sodium bicarbonate water

생성물 1

HCID 66839333(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-[2-oxo-3-(3,4,5-trifluorophenyl)piperidin-1-yl]acrylamide수율 50.6%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

IPEA (0.41 mL), HOBT (105 mg) and EDC (149 mg) were added to a solution of 1-amino-3-(3,4,5-trifluorophenyl)piperidin-2-one hydrochloride (109 mg) and (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (100 mg) in DMF (2 mL), and the reaction solution was stirred at room temperature for three hours. Ethyl acetate and saturated sodium bicarbonate water 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 (elution solvent: ethyl acetate->ethyl acetate:methanol=5:1) to obtain 95 mg 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 (elution solvent: ethyl acetate->ethyl acetate:methanol=5:1)

출처 및 근거

ORD 기록
ord-bad3c3eb8daa4b4ab82566be194204fa
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713993B2

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