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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
ノート
印刷プレビュー

反応式

HRID 1922300 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
190 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cb9298a86c6e4bd8bb0ebb49d3354dbb
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08173820B2

反応ノート

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