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Sulfuric acid magnesium salt (1:1) → {2-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]propyl}-(4-pyridin-4-yl-butyl)amine

HRID 1458370
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HRID 1458370 반응식
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH:10]=O)=[CH:3][CH:2]=1.[CH3:12][C:13]1[CH:14]=[C:15]([C:20]2[NH:21][C:22]3[C:27]([C:28]=2[CH:29]([CH3:32])[CH2:30][NH2:31])=[CH:26][C:25]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:24][CH:23]=3)[CH:16]=[C:17]([CH3:19])[CH:18]=1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>>[CH3:19][C:17]1[CH:16]=[C:15]([C:20]2[NH:21][C:22]3[C:27]([C:28]=2[CH:29]([CH3:32])[CH2:30][NH:31][CH2:10][CH2:9][CH2:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:26][C:25]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:24][CH:23]=3)[CH:14]=[C:13]([CH3:12])[CH:18]=1
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참가 물질

5

반응물 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 114464344-Pyridin-4-ylbutanalHCID 221009152-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]propylamine

생성물 1

HCID 22100895{2-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]propyl}-(4-pyridin-4-yl-butyl)amine수율 42.2%

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온도
-5 °C

실험 절차

A mixture of 4-pyridin-4-yl-butyraldehyde (23 mg), 2-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]propylamine (50 mg) and magnesium sulfate (76 mg) were diluted with 1.5 mL CDCl3 and stirred at -5° C. After 15 minutes, a solution of sodium borohydride (6.8 mg in 1.5 mL dry methanol) were added and the mixture stirred at low temperature for an additional 20 minutes. At this time the reaction was quenched by the addition of water, extracted with ethyl acetate and the organic portion washed sequentially with water and brine then dried over sodium sulfate. Purification of the concentrate by preparative TLC on silica gel (methylene chloride:methanol, 9:1) gave the title compound (29 mg).

후처리

  1. additionwere diluted with 1.5 mL CDCl3
  2. stirringthe mixture stirred at low temperature for an additional 20 minutes
  3. customAt this time the reaction was quenched by the addition of water
  4. extractionextracted with ethyl acetate
  5. washthe organic portion washed sequentially with water and brine
  6. dry with materialthen dried over sodium sulfate
  7. customPurification of the
  8. concentrationconcentrate by preparative TLC on silica gel (methylene chloride:methanol, 9:1)

출처 및 근거

ORD 기록
ord-0d3758a6a3f04a7d89192f9dedee5088
출처 데이터셋
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05849764

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