Diisopropylethylamine → (E)-N-[3-(3,4-difluorophenyl)-2-oxopiperidin-1-yl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylamide

HRID 599629ノート

反応式

HRID 599629 の反応式
C(N(C(C)C)CC)(C)C.[NH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=2)[C:12]1=[O:25].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[CH3:41][O:42][C:43]1[CH:44]=[C:45](/[CH:55]=[CH:56]/[C:57](O)=[O:58])[CH:46]=[CH:47][C:48]=1[N:49]1[CH:53]=[C:52]([CH3:54])[N:51]=[CH:50]1>C(Cl)Cl.O>[F:24][C:19]1[CH:18]=[C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][N:11]([NH:10][C:57](=[O:58])/[CH:56]=[CH:55]/[C:45]3[CH:46]=[CH:47][C:48]([N:49]4[CH:53]=[C:52]([CH3:54])[N:51]=[CH:50]4)=[C:43]([O:42][CH3:41])[CH:44]=3)[C:12]2=[O:25])[CH:22]=[CH:21][C:20]=1[F:23]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 668393321-Amino-3-(3,4-difluorophenyl)piperidin-2-one

生成物 1

HCID 67067196(E)-N-[3-(3,4-difluorophenyl)-2-oxopiperidin-1-yl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylamide収率 70.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

IPEA (1.5 mL), 1-amino-3-(3,4-difluorophenyl)piperidin-2-one (420 mg) and BOPCl (0.53 g) were added to a solution of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (450 mg) in methylene chloride (15 mL) at room temperature, and the reaction solution was stirred at room temperature for three hours. Water was added to the reaction solution, followed by extraction with chloroform. The resulting extract was washed with a saturated sodium chloride solution. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system, then ethyl acetate-methanol system) to obtain 572 mg of the title compound. The property value of the compound is as follows.

後処理

  1. extractionfollowed by extraction with chloroform
  2. extractionThe resulting extract
  3. washwas washed with a saturated sodium chloride solution
  4. dry with materialThe resulting organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (carrier
  7. washelution solvent

出典と根拠

ORDレコード
ord-b8445cc797d6416791bef629fb232412
出典データセット
uspto-grants-2011_03
特許番号
US07897632B2

反応ノート

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