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Cyclopropylacetylene → 7-chloro-3-(cyclopropylethynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1606990
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1606990
[Cl:1][C:2]1[C:7]2[C:8](=[O:18])[N:9]([CH3:17])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3I)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:19]1([C:22]#[CH:23])[CH2:21][CH2:20]1>C(NCC)C.C(Cl)CCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[C:7]2[C:8](=[O:18])[N:9]([CH3:17])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:23]#[C:22][CH:19]3[CH2:21][CH2:20]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 2

HCID 138823CyclopropylacetyleneHCID 198306597-chloro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Produkt 1

HCID 198515147-chloro-3-(cyclopropylethynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator
HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 111,2-DichloroethaneLösungsmittel
HCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

3.37 g (10 mmol) of 7-chloro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was heated to 75° for 16 hours with 1.47 g of cyclopropylacetylene, 70 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 20 mg of copper(I) iodide in 20 ml of diethylamine and 10 ml of ethylene chloride. By evaporation of the reaction mixture and chromatography of the residue on silica gel while eluting with ethyl acetate there was obtained a mixture of product and starting material. In order to remove the starting material, the mixture was heated under reflux for 4 hours with 1 ml of 2-methyl-3-butyn-2-ol, 70 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 20 mg of copper(I) iodide in 10 ml of diethylamine and 10 ml of ethylene chloride. By evaporation of the reaction mixture and chromatography of the residue on silica gel while eluting with ethyl acetate the byproduct can be separated from the desired product. After crystallization from ethyl acetate there was obtained 7-chloro-3-(cyclopropylethynyl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 177°-178°.

Aufarbeitung

  1. customBy evaporation of the reaction mixture and chromatography of the residue on silica gel
  2. washwhile eluting with ethyl acetate
  3. customthere was obtained
  4. additiona mixture of product
  5. customIn order to remove the starting material
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 4 hours with 1 ml of 2-methyl-3-butyn-2-ol, 70 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 20 mg of copper(I) iodide in 10 ml of diethylamine and 10 ml of ethylene chloride
  8. customBy evaporation of the reaction mixture and chromatography of the residue on silica gel
  9. washwhile eluting with ethyl acetate the byproduct
  10. customcan be separated from the desired product
  11. customAfter crystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3c95c1d79ed44b299f1136040214473c
Quelldatensatz
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04863920

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