1-(Prop-2-yn-1-yl)-1H-indole-2,3-dione → 1-[3-[6-(2-Chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a]-[1,4]benzodiazepin-8-yl]-2-propynyl]-1H-indole-2,3-dione

HRID 1032751

Reaktionsgleichung

Reaktionsgleichung von HRID 1032751
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16](I)[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.[CH2:24]([N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](=[O:36])[C:28]1=[O:37])[C:25]#[CH:26]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([C:26]#[C:25][CH2:24][N:27]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29](=[O:36])[C:28]3=[O:37])[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1

Komponenten

3

Edukt 2

HCID 19090021-(Prop-2-yn-1-yl)-1H-indole-2,3-dioneHCID 148518946-(2-chlorophenyl)-8-iodo-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine

Produkt 1

HCID 148518381-[3-[6-(2-Chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a]-[1,4]benzodiazepin-8-yl]-2-propynyl]-1H-indole-2,3-dione

Versuchsvorschrift

This compound was prepared by reacting 6-(2-chlorophenyl)-8-iodo-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine with 1-(2-propynyl)-1H-indole-2,3-dione [ref. A. Lindquist, p. Lagerstrom and R. Dahlbom, Acta Pharm. Suecica 9, 99 (1972)] as described in Example 9. The crude product was purified by chromatography over 40 fold amount of silica gel using 5% (V/V) of ethanol in methylene chloride. Crystallization from ethyl acetate qave yellow crystals of 1-[3-[6-(2-chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-8-yl]-2-propynyl]-1H-indole 2,3-dione with m.p. 210°-212° C. These crystals contained according to microanalysis and pmr-spectrum 0.25 molar amounts of ethyl acetate.

Aufarbeitung

  1. customThis compound was prepared
  2. customThe crude product was purified by chromatography over 40 fold amount of silica gel using 5% (V/V) of ethanol in methylene chloride
  3. customCrystallization from ethyl acetate qave yellow crystals of 1-[3-[6-(2-chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-8-yl]-2-propynyl]-1H-indole 2,3-dione with m.p. 210°-212° C

Quellen und Nachweise

ORD-Eintrag
ord-22a276a9e82b4dabb9a52f4c4a67cbfa
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04959361

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