Chloroacetic anhydride → (S)-8-bromo-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

HRID 1378167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378167
[Br:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](=[N:18][OH:19])[NH2:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:23][CH2:24][C:25](OC(=O)CCl)=O>CN(C)C=O>[Br:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:17]=[C:25]([CH2:24][Cl:23])[O:19][N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 10946Chloroacetic anhydrideHCID 53634407(S)-8-bromo-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime

Produkt 1

HCID 53678825(S)-8-bromo-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-oneAusbeute 65,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

7 g (19.3 mmol) of (S)-8-bromo-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carboxamidoxime were stirred with 3.8 g (22.2 mmol) of chloroacetic anhydride in 50 ml of N,N-dimethylformamide at room temperature for 1 hour and at 105° for 2 hours. After evaporating the reaction mixture the residue was dissolved in methylene chloride and the solution was washed with saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate and concentrated. After recrystallizing the residue from methanol there were obtained 5.3 g (65%) of (S)-8-bromo-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of m.p. 210°-211°.

Aufarbeitung

  1. customAfter evaporating the reaction mixture the residue
  2. dissolutionwas dissolved in methylene chloride
  3. washthe solution was washed with saturated sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customAfter recrystallizing the residue from methanol

Quellen und Nachweise

ORD-Eintrag
ord-eb49f4a982d24f27b5f33de67846e91b
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05665718

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