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N,N-Dimethylglycine → N-{(2S)-5-[(6-methyl-3-pyridinyl)oxy]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide

HRID 1922300
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HRID 1922300 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.[CH3:18][C:19]1[N:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O>CS(C)=O.[Cu]I>[CH3:18][C:19]1[N:24]=[CH:23][C:22]([O:25][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]3)=[CH:21][CH:20]=1
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참가 물질

7

반응물 4

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 142752-Methyl-5-hydroxypyridineHCID 46899974(S)-N-(5-bromo-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

생성물 1

HCID 44124719N-{(2S)-5-[(6-methyl-3-pyridinyl)oxy]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide수율 23.3%

시약·촉매·용매 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 679Dimethyl Sulfoxide용매

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온도
190 °C

실험 절차

A reaction mixture of N-[(2S)-5-bromo-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (100 mg, 0.31 mmol, Description 1), 6-methyl-3-pyridinol (35 mg, 0.32 mmol), caesium carbonate (308 mg, 0.94 mmol), copper(I) iodide (66 mg, 0.35 mmol) and N,N-dimethylglycine (39 mg, 0.38 mmol) in DMSO (1.5 ml) was heated in a microwave at 190° C. for 30 minutes. The reaction mixture was then partitioned between dichloromethane and water and the organic solution was dried (MgSO4) and evaporated under reduced pressure to yield the crude product. The crude product was purified using MDAP. The resulting solution was diluted with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic solution was dried (MgSO4) and evaporated under reduced pressure to obtain the title compound as a yellow gum (25 mg).

후처리

  1. customThe reaction mixture was then partitioned between dichloromethane and water
  2. dry with materialthe organic solution was dried (MgSO4)
  3. customevaporated under reduced pressure
  4. customto yield the crude product
  5. customThe crude product was purified
  6. additionThe resulting solution was diluted with saturated aqueous sodium bicarbonate solution
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic solution was dried (MgSO4)
  9. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-cb9298a86c6e4bd8bb0ebb49d3354dbb
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08173820B2

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