1,4-Dioxane → {8-chloro-2-ethyl-4-oxo-3-[4-(pyrrolidine-1-carbonyl)benzyl]-1,4-dihydroquinolin-5-yloxy}acetic Acid Methyl Ester

HRID 2266617노트

반응식

HRID 2266617 반응식
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([NH2:13])[CH:7]=1.C[O:16][C:17](=O)[CH:18]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[O:31])=[CH:26][CH:25]=1)[C:19](=O)[CH2:20][CH3:21].O1CCOCC1>O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]2[C:7]=1[C:17](=[O:16])[C:18]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([N:32]3[CH2:33][CH2:34][CH2:35][CH2:36]3)=[O:31])=[CH:26][CH:25]=1)=[C:19]([CH2:20][CH3:21])[NH:13]2

참가 물질

5

반응물 3

HCID 312751,4-DioxaneHCID 66717604Methyl 2-(3-amino-4-chlorophenoxy)acetateHCID 687803523-oxo-2-[4-(pyrrolidine-1-carbonyl)benzyl]pentanoic Acid Methyl Ester

생성물 1

HCID 68782062{8-chloro-2-ethyl-4-oxo-3-[4-(pyrrolidine-1-carbonyl)benzyl]-1,4-dihydroquinolin-5-yloxy}acetic Acid Methyl Ester

시약·촉매·용매 1

HCID 962Water용매

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온도
120 °C

실험 절차

A mixture of (3-amino-4-chlorophenoxy)acetic acid methyl ester (1.0 g), 3-oxo-2-[4-(pyrrolidine-1-carbonyl)benzyl]pentanoic acid methyl ester (1.9 g), polyphosphoric acid (6.0 g) and dioxane (20 mL) was heated at 120° C. for 18 hours. The mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane, ethyl acetate and methanol (9:1:0 to 0:9:1 by volume) to afford title compound, 0.079 g.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customthe solvent removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with a mixture of dichloromethane, ethyl acetate and methanol (9:1:0 to 0:9:1 by volume)

출처 및 근거

ORD 기록
ord-d583dd2a3a7943dca0fd22df65d87774
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858640B2

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