Sodium Carbonate → 2-(4-Cyanophenylaminomethyl)-1-methyl-5-[1-(2-tert.butyloxycarbonyl-azetidin-1-yl)-1-(pyrrolidin-1-yl-carbonyl)-ethyl]-benzimidazole

HRID 1067475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1067475
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([C:21]([NH2:30])([C:23]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:24])[CH3:22])=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2].Br[CH:32]([CH2:40][CH2:41]Br)[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([C:21]([N:30]4[CH2:41][CH2:40][CH:32]4[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([C:23]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:24])[CH3:22])=[CH:20][C:13]=3[N:12]=2)=[CH:7][CH:8]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 5107723tert-Butyl 2,4-dibromobutyrateHCID 181881512-(4-Cyanophenylaminomethyl)-1-methyl-5-[1-amino-1-(pyrrolidin-1-yl-carbonyl)-ethyl]-benzimidazole

Produkt 1

HCID 700832612-(4-Cyanophenylaminomethyl)-1-methyl-5-[1-(2-tert.butyloxycarbonyl-azetidin-1-yl)-1-(pyrrolidin-1-yl-carbonyl)-ethyl]-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

0.8 g (1.86 mmol) of 2-(4-cyanophenylaminomethyl)-1-methyl-5-[1-amino-1-(pyrrolidin-1-yl-carbonyl)-ethyl]-benzimidazole and 1.65 g ((5.5 mmol) of tert.butyl 2,4-dibromobutyrate are dissolved in 5 ml of ethanol, mixed with 0.2 g (1.86 mmol) of sodium carbonate and stirred under nitrogen for 30 hours at 55° C. After cooling, the white precipitate is filtered off and washed with ethanol. The filtrate is concentrated by evaporation, the residue is chromatographed on silica gel, eluting with ethyl acetate and ethyl acetate/ethanol/ammonia (20:1:0.01). The desired fractions are combined and concentrated by evaporation.

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe white precipitate is filtered off
  3. washwashed with ethanol
  4. concentrationThe filtrate is concentrated by evaporation
  5. customthe residue is chromatographed on silica gel
  6. washeluting with ethyl acetate and ethyl acetate/ethanol/ammonia (20:1:0.01)
  7. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-cdde9183850f4850b2f6a85ea4b02431
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248770B1

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