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Dipropylamine → (S)-1-(5-dipropylaminomethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a]-[1,4]benzodiazepin-9-one

HRID 1378082
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1378082
[CH2:1]([NH:4][CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].Cl[CH2:9][C:10]1[O:14][C:13]([C:15]2[N:16]=[CH:17][N:18]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[C:22](=[O:29])[N:21]4[CH2:30][CH2:31][C@H:20]4[C:19]=23)=[N:12][N:11]=1>CN(C)C=O>[CH2:1]([N:4]([CH2:9][C:10]1[O:14][C:13]([C:15]2[N:16]=[CH:17][N:18]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[C:22](=[O:29])[N:21]4[CH2:30][CH2:31][C@H:20]4[C:19]=23)=[N:12][N:11]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]
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Komponenten

4

Edukt 2

HCID 8902DipropylamineHCID 53723128(S)-1-(5-chloromethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

Produkt 1

HCID 53964145(S)-1-(5-dipropylaminomethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a]-[1,4]benzodiazepin-9-oneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.94 ml (73 mmol) of dipropylamine was added to a solution of 1.17 g (3.42 mmol) of (S)-1-(5-chloromethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one in 10 ml of dimethylformamide, whereupon the mixture was stirred at room temperature for 12 hours. The dimethylformamide was evaporated and the residue was partitioned between methylene chloride and 2N sodium carbonate solution. The aqueous phase was washed twice with methylene chloride and the organic phases were dried with sodium sulfate, filtered and evaporated. Chromatography (silica gel, methylene chloride/methanol 95:5) yielded 0.900 g (65%) of (S)-1-(5-dipropylaminomethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a]-[1,4]benzodiazepin-9-one as a colourless foam, Rf=0.46 (silica gel, methylene chloride/methanol 95:5).

Aufarbeitung

  1. customThe dimethylformamide was evaporated
  2. customthe residue was partitioned between methylene chloride and 2N sodium carbonate solution
  3. washThe aqueous phase was washed twice with methylene chloride
  4. dry with materialthe organic phases were dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-86c65fd00cbf4277830396238a3d928f
Quelldatensatz
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05665718

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