Dimethylformamide → 7-chloro-3-(4-dipropylaminomethyl-thiazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo(1,5-a][1,4]benzodiazepin-6-one

HRID 1737356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1737356
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[S:17][CH:18]=[C:19]([CH2:21]Cl)[N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:25]([NH:28][CH2:29][CH2:30][CH3:31])[CH2:26][CH3:27].CN(C)C=O>O1CCCC1>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[S:17][CH:18]=[C:19]([CH2:21][N:28]([CH2:29][CH2:30][CH3:31])[CH2:25][CH2:26][CH3:27])[N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 8902DipropylamineHCID 218423077-chloro-3-(4-chloromethyl-thiazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Produkt 1

HCID 218422467-chloro-3-(4-dipropylaminomethyl-thiazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo(1,5-a][1,4]benzodiazepin-6-oneAusbeute 44,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of 1.0 g (0.00263 mol) of 7-chloro-3-(4-chloromethyl-thiazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 60 ml of tetrahydrofuran was treated with 7.2 ml (0.0527 mol) of dipropylamine and 5 ml of dimethylformamide. After stirring at reflux for 16 hrs. the suspension obtained was filtered and the solution was completely freed from the solvents. The residue was chromatographed over silica gel with ethyl acetate as the eluent and recrystallized from hot isopropyl ether. There was obtained 0.52 g (44%) of 7-chloro-3-(4-dipropylaminomethyl-thiazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo(1,5-a][1,4]benzodiazepin-6-one as white crystals; m.p. 121-123°.

Aufarbeitung

  1. temperatureat reflux for 16 hrs
  2. customthe suspension obtained
  3. filtrationwas filtered
  4. customThe residue was chromatographed over silica gel with ethyl acetate as the eluent
  5. customrecrystallized from hot isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f5fe6ba5635c44d78aa62e2cede9f2fd
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05962450

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