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Water → 7-chloro-3-[3-(cyclopropyl-methoxy)-1-propynyl]-4,5-dihydro-5 methyl6H-imidazo-[1,5-a][1,4]benzodiazepin-6-one

HRID 1493121
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1493121
[OH-].[K+].[Cl:3][C:4]1[C:9]2[C:10](=[O:23])[N:11]([CH3:22])[CH2:12][C:13]3[N:14]([CH:15]=[N:16][C:17]=3[C:18]#[C:19][CH2:20][OH:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1.Br[CH2:25][CH:26]1[CH2:28][CH2:27]1.O>CN(C)C=O>[Cl:3][C:4]1[C:9]2[C:10](=[O:23])[N:11]([CH3:22])[CH2:12][C:13]3[N:14]([CH:15]=[N:16][C:17]=3[C:18]#[C:19][CH2:20][O:21][CH2:25][CH:26]3[CH2:28][CH2:27]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 81503BromomethylcyclopropaneHCID 100405557-chloro-4,5-dihydro-3-(3-hydroxy-1-propynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Produkt 1

HCID 100437977-chloro-3-[3-(cyclopropyl-methoxy)-1-propynyl]-4,5-dihydro-5 methyl6H-imidazo-[1,5-a][1,4]benzodiazepin-6-oneAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3.34 g (59 mmol) of freshly powdered potassium hydroxide were suspended in 25 ml of N,N-dimethylformamide and treated with 4.0 g (13.2 mmol) of 7-chloro-4,5-dihydro-3-(3-hydroxy-1-propynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one. After stirring at room temperature for 5 minutes the mixture was cooled to 2°, whereupon 4.95 g (31.1 mmol) of bromomethylcyclopropane were added thereto. The reaction mixture was stirred at room temperature for 1 hour and then poured into water. The mixture was extracted three times with methylene chloride, the combined organic extracts were washed with water, dried over magnesium sulfate and evaporated. By crystallization of the residue from ethyl acetate and ether there were obtained 4.0 g (84%) of 7-chloro-3-[3-(cyclopropyl-methoxy)- 1-propynyl]-4,5-dihydro-5 methyl6H-imidazo-[1,5-a][1,4]benzodiazepin-6-one of melting point 124-126°.

Aufarbeitung

  1. additionwere added
  2. stirringThe reaction mixture was stirred at room temperature for 1 hour
  3. extractionThe mixture was extracted three times with methylene chloride
  4. washthe combined organic extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customBy crystallization of the residue from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ca04ddd4043f4da1b3b0855929fe2b7f
Quelldatensatz
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05021411

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