Sodium triacetoxyborohydride → methyl 3-[4-(7-chloro-2-(methylsulfanyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoate

HRID 1877805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1877805
[CH3:1][C:2]([CH3:9])([CH:7]=O)[C:3]([O:5][CH3:6])=[O:4].[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[N:20]=[C:19]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:18]3=[CH:27][C:28]([S:30][CH3:31])=[CH:29][N:17]3[CH2:16][C:15]=2[CH:32]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[N:20]=[C:19]([N:21]3[CH2:26][CH2:25][N:24]([CH2:7][C:2]([CH3:1])([CH3:9])[C:3]([O:5][CH3:6])=[O:4])[CH2:23][CH2:22]3)[C:18]3=[CH:27][C:28]([S:30][CH3:31])=[CH:29][N:17]3[CH2:16][C:15]=2[CH:32]=1

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11137194Methyl 2,2-dimethyl-3-oxopropanoateHCID 681561457-chloro-2-(methylsulfanyl)-11-(piperazin-1-yl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Produkt 1

HCID 68156134methyl 3-[4-(7-chloro-2-(methylsulfanyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoateAusbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Add methyl 2,2-dimethyl-3-oxo-propanoate (0.928 g, 7.13 mmoles) in DCM (5 mL) to 7-chloro-2-(methylsulfanyl)-11-(piperazin-1-yl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine (1.0 g, 2.85 mmoles) in DCM (10 mL) and stir under nitrogen for 30 minutes at room temperature. Add sodium triacetoxyborohydride (3 equiv; 1.89 g, 8.56 mmoles) to the reaction mixture and stir under nitrogen overnight at room temperature. Add methanol and apply to an SCX-2 column, wash with methanol and elute with 2M ammonia in methanol. Evaporate the methanol solution to give methyl 3-[4-(7-chloro-2-(methylsulfanyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoate (1.23 g, 84%). MS (m/z): 461.12 (M+1).

Aufarbeitung

  1. washAdd methanol and apply to an SCX-2 column, wash with methanol
  2. washelute with 2M ammonia in methanol
  3. customEvaporate the methanol solution

Quellen und Nachweise

ORD-Eintrag
ord-f052e7e9573a4affa130c2938d5ca401
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314092B2

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