Sodium Iodide → (3RS)-2,3-dihydro-1-(isoquinolin-1-yl)methyl-5-phenyl-3-phthalimido-1H-1,4-benzodiazepin-2-one

HRID 963481Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963481
[H-].[Na+].[C:3]1([C:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12](=[O:20])[CH:11]([N:21]3[C:25](=[O:26])[C:24]4=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]4[C:22]3=[O:31])[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[I-].[Na+].Cl[CH2:35][C:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][N:37]=1>CN(C)C=O>[C:36]1([CH2:35][N:13]2[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[N:10][CH:11]([N:21]3[C:22](=[O:31])[C:23]4=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]4[C:25]3=[O:26])[C:12]2=[O:20])[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][N:37]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 132210311-(Chloromethyl)isoquinolineHCID 14800302(3RS)-1,3-dihydro-5-phenyl-3-phthalimido-2H-1,4-benzodiazepine-2-one

Produkt 1

HCID 19081216(3RS)-2,3-dihydro-1-(isoquinolin-1-yl)methyl-5-phenyl-3-phthalimido-1H-1,4-benzodiazepin-2-oneAusbeute 39,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (0.11 g in a 64% dispersion of mineral oil) in dry N,N-dimethylformamide (20 ml) was added slowly (3RS)-2,3-dihydro-5-phenyl-3-phthalimido-1H-1,4-benzodiazepin-2-one (1.00 g) at ambient temperature, and stirred for 2 hours. To the mixture was added sodium iodide (0.413 g) and followed dropwise a solution of 1-chloromethylisoquinoline (0.695 g) in dry N.N-dimethylformamide (5 ml) at ambient temperature and stirred overnight. The mixture was concentrated in vacuo and the residue was taken up with ethyl acetate. The organic layer was washed with saturated sodium carbonate aqueous solution, and dried over sodium sulfate, filtered and concentrated in vacuo to give a crude product. The crude product was purified by column chromatography with chloroform as an eluent to give (3RS)-2,3-dihydro-1-(isoquinolin-1-yl)methyl-5-phenyl-3-phthalimido-1H-1,4-benzodiazepin-2-one (0.54 g) as a colorless form.

Aufarbeitung

  1. customat ambient temperature
  2. stirringstirred overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. washThe organic layer was washed with saturated sodium carbonate aqueous solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude product
  9. customThe crude product was purified by column chromatography with chloroform as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-25bde1368e6744a083dcaad24c04bb8b
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763437

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