(S)-8-chloro-7-fluoro-12,12a-dihydro-1-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one → (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

HRID 1378057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378057
[Cl:1][C:2]1[C:7]2[C:8](=[O:35])[N:9]3[CH2:34][CH2:33][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:20][N:19]=[C:18]([CH2:21][N:22]4C(=O)C5=CC=CC=C5C4=O)[N:17]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[F:36]>CN>[NH2:22][CH2:21][C:18]1[N:17]=[C:16]([C:15]2[N:14]=[CH:13][N:12]3[C:6]4[CH:5]=[CH:4][C:3]([F:36])=[C:2]([Cl:1])[C:7]=4[C:8](=[O:35])[N:9]4[CH2:34][CH2:33][C@H:10]4[C:11]=23)[O:20][N:19]=1

Komponenten

3

Edukt 1

HCID 53878056(S)-8-chloro-7-fluoro-12,12a-dihydro-1-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

Produkt 1

HCID 53728112(S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-oneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6329MethylamineLösungsmittel

Versuchsvorschrift

16 g (31.85 mmol) of (S)-8-chloro-7-fluoro-12,12a-dihydro-1-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one were treated with 100 ml of methylamine (33% in ethanol). The solution was stirred at 70° for 1 hour and subsequently cooled. The suspension obtained was filtered and the crystallizate was partially dissolved in 100 ml of methylene chloride. By filtering and evaporating the filtrate there were obtained 11.7 g (99%) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was used without further purification as the starting material for the Example described hereinafter.

Aufarbeitung

  1. temperaturesubsequently cooled
  2. customThe suspension obtained
  3. filtrationwas filtered
  4. dissolutionthe crystallizate was partially dissolved in 100 ml of methylene chloride
  5. filtrationBy filtering
  6. customevaporating the filtrate there

Quellen und Nachweise

ORD-Eintrag
ord-40e9c8a610eb47cd939e270dc9cd6132
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05665718

Notizen zur Reaktion

Wird geladen…