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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
ノート
印刷プレビュー

反応式

HRID 546739 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 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

生成物 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]acrylamide収率 90.4%

試薬・触媒・溶媒 4

HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a82882278a2541cc9bcfdbe2574dcf9d
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07935815B2

反応ノート

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