Triethylamine → 1,2-Dihydro-8-(dimethylamino)methylbenzo[b]pyrrolo[3,2,1-jk][1,2,4]triazolo[4,3-d][1,4]benzodiazepine

HRID 2050999

Reaktionsgleichung

Reaktionsgleichung von HRID 2050999
[CH2:1]1[N:12]2[C:13]3[C:3](=[CH:4][CH:5]=[CH:6][C:7]=3[C:8](=S)[NH:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=32)[CH2:2]1.Cl.CN(C[C:24]([NH:26][NH2:27])=O)C.[CH2:28]([N:30]([CH2:33]C)[CH2:31]C)C>CN(C)C=O>[CH3:28][N:30]([CH2:33][C:15]1[CH:16]=[CH:17][C:10]2[N:9]3[CH:24]=[N:26][N:27]=[C:8]3[C:7]3[CH2:6][CH2:5][CH:4]=[C:3]4[CH:2]=[CH:1][N:12]([C:13]=34)[C:11]=2[CH:14]=1)[CH3:31]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 68318N,N-Dimethylglycine hydrazide hydrochlorideHCID 15132539HCID 15132539, Verbindung

Produkt 1

HCID 679230661,2-Dihydro-8-(dimethylamino)methylbenzo[b]pyrrolo[3,2,1-jk][1,2,4]triazolo[4,3-d][1,4]benzodiazepineAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1,2-Dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin6-thione (4 g) was added to a solution of dimethylaminoacetic hydrazide hydrochloride (2 g) and triethylamine (2.4 ml) in dimethylformamide (25 ml). The mixture was refluxed overnight, cooled, and concentrated under reduced pressure. The residue was purified by high performance liquid chromatography (2.5% methano/dichloromethane). The appropriate fractions were triturated with dry ether to yield 2.4 g (47.2%) of product, mp 164°-165° C.

Aufarbeitung

  1. temperatureThe mixture was refluxed overnight
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by high performance liquid chromatography (2.5% methano/dichloromethane)
  5. customThe appropriate fractions were triturated with dry ether

Quellen und Nachweise

ORD-Eintrag
ord-261a1c550af5459ba45f8471822a41d2
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05015738

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