Water → 3-(4-fluorophenyl)-3-methoxy-3-(5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-2H-[1,2,4]triazol-3-yl)propan-1-ol

HRID 599618ノート

反応式

HRID 599618 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:16][CH3:17])([CH2:13][CH2:14][OH:15])[C:9]([NH:11][NH2:12])=O)=[CH:4][CH:3]=1.Cl.Cl.[CH3:20][O:21][C:22]1[CH:23]=[C:24](/[CH:34]=[CH:35]/[C:36](=[NH:40])OCC)[CH:25]=[CH:26][C:27]=1[N:28]1[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]1.C(OCC)(=O)C.O>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:16][CH3:17])([C:9]2[NH:11][N:12]=[C:36](/[CH:35]=[CH:34]/[C:24]3[CH:25]=[CH:26][C:27]([N:28]4[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]4)=[C:22]([O:21][CH3:20])[CH:23]=3)[N:40]=2)[CH2:13][CH2:14][OH:15])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 66838954ethyl(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylimidate dihydrochlorideHCID 670673452-(4-Fluorophenyl)-4-hydroxy-2-methoxybutyric acid hydrazide

生成物 1

HCID 670672233-(4-fluorophenyl)-3-methoxy-3-(5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-2H-[1,2,4]triazol-3-yl)propan-1-ol収率 49.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
75 °C

実験手順

A solution of 2-(4-fluorophenyl)-4-hydroxy-2-methoxybutyric acid hydrazide (40 mg) in ethanol (1.6 mL) was added to a solution of ethyl(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylimidate dihydrochloride (65 mg) and TEA (0.12 mL) in ethanol (0.7 mL), and the reaction solution was stirred at 75° C. for two days. The reaction solution was left to cool to room temperature. Then, ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate-methanol system) to obtain 38 mg of the title compound. The property value of the compound is as follows.

後処理

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. customthe organic layer was separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate-methanol system)

出典と根拠

ORDレコード
ord-99072cb13c83476eb5c643ee3b7bab78
出典データセット
uspto-grants-2011_03
特許番号
US07897632B2

反応ノート

読み込み中…