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Pyridine → 5-[1-(4-Methanesulfonylaminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

HRID 1811455
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반응식

HRID 1811455 반응식
ClCCl.[NH2:4][C:5]1[CH:32]=[CH:31][C:8]([CH2:9][N:10]2[C:19]3[C:14](=[C:15]([CH2:22][CH:23]4[S:27][C:26](=[O:28])[NH:25][C:24]4=[O:29])[CH:16]=[CH:17][C:18]=3[O:20][CH3:21])[CH2:13][CH2:12][C:11]2=[O:30])=[CH:7][CH:6]=1.N1C=CC=CC=1.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>O>[CH3:39][S:40]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:19]3[C:14](=[C:15]([CH2:22][CH:23]4[S:27][C:26](=[O:28])[NH:25][C:24]4=[O:29])[CH:16]=[CH:17][C:18]=3[O:20][CH3:21])[CH2:13][CH2:12][C:11]2=[O:30])=[CH:31][CH:32]=1)(=[O:42])=[O:41]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 866139395-[1-(4-Aminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

생성물 1

HCID 580267035-[1-(4-Methanesulfonylaminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione수율 92%

시약·촉매·용매

1
HCID 962Water용매

실험 절차

To a dichloromethane (20 ml) solution of 1.00 g (0.00243 mM) of 5-[1-(4-aminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione were successively added pyridine (2.0 ml) and 0.21 ml (0.0027 mM) of methanesulfonyl chloride under ice cooling with stirring. The mixture was stirred at the same temperature for 30 minutes, and water was added to stop the reaction. The resultant was washed (twice with water and once with saturated sodium chloride solution), dried (magnesium sulfate), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=1:10→1:1), giving 1.1 g (92% yield) of the target compound as a white amorphous solid.

후처리

  1. stirringThe mixture was stirred at the same temperature for 30 minutes
  2. customthe reaction
  3. washThe resultant was washed (twice with water
  4. dry with materialonce with saturated sodium chloride solution), dried (magnesium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=1:10→1:1)

출처 및 근거

ORD 기록
ord-89606fe7098e4b61968cdbe2492d93b8
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362252B2

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