Potassium Carbonate → 2-(5-Chloro-2-(2-[4-(4-Fluoro-Benzyl)-(2R,5S)-2,5-Dimethyl-Piperazin-1-Yl]-2-Oxo-Ethoxy}-Phenoxy)-Nicotinic Acid

HRID 11704

反応式

HRID 11704 の反応式
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][C@H:11]2[CH3:25])=[O:9])=[C:4]([OH:28])[CH:3]=1.Cl[C:30]1[N:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([OH:34])=[O:33].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.[Cu].[Cu]I>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][C@H:11]2[CH3:25])=[O:9])=[C:4]([CH:3]=1)[O:28][C:30]1[N:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([OH:34])=[O:33]

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 762582-Chloronicotinic acidHCID 537887242-(4-Chloro-2-hydroxy-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

生成物 1

HCID 696553562-(5-Chloro-2-(2-[4-(4-Fluoro-Benzyl)-(2R,5S)-2,5-Dimethyl-Piperazin-1-Yl]-2-Oxo-Ethoxy}-Phenoxy)-Nicotinic Acid

試薬・触媒・溶媒 4

HCID 23978Copper触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
145 °C

実験手順

To a solution of 2-(4-chloro-2-hydroxy-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.10 g, 0.25 mmol), and 2-chloro-nicotinic acid (0.045 g, 0.28 mmol) in dimethylformamide (0.75 mL) were added potassium carbonate (0.084 g, 0.60 mmol), copper (0.0050 g, 0.078 mmol) and copper (I) iodide (0.0050 g, 0.0.026 mmol). The resulting mixture was stirred at 145° C. for 2 hours. The reaction was cooled and diluted with ethyl acetate and washed with water. The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuo. Chromatography on silica gel followed by trituration with methylene chloride/hydrogen chloride in diethyl ether gave the title compound as the hydrochloride salt (0.022 g, LRMS 528.4, 530.4).

後処理

  1. temperatureThe reaction was cooled
  2. washwashed with water
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a2b9b19a08364319a45c2b02891efc83
出典データセット
uspto-grants-2006_08
特許番号
US07098212B2

関連ノート

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