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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
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인쇄 미리보기

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HRID 11704 반응식
[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]
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참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 4

HCID 23978
Copper
촉매
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

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온도
145 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a2b9b19a08364319a45c2b02891efc83
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07098212B2

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