Dimethylformamide → HCID 18464882, Verbindung

HRID 1584501Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1584501
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)C=O.[H-].[Na+].[CH3:31][O:32][CH2:33][CH2:34]Cl>ClCCl.ClCCl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]([CH2:34][CH2:33][O:32][CH3:31])[C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 184646551-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane

Produkt 1

HCID 18464882HCID 18464882, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepane (2.03 g, 6.41 mmol) and dimethylformamide (50 mL). Cool in an ice-bath. Add sodium hydride (0.28 g, 60% in oil, 7.0 mmol). After 20 minutes, add 2-chloroethyl methyl ether (0.7 mL, 7.66 mmol). Heat to 85° C. After 18 hours, cool to ambient temperature and dilute with dichloromethane, and extract with water, a saturated aqueous sodium bicarbonate solution, and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with dichloromethane/methanol/concentrated ammonium hydroxide 95/5/0.05 to give 1-(t-butoxycarbonyl)-4-(1-(2-methoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane.

Aufarbeitung

  1. temperatureCool in an ice-bath
  2. waitAfter 18 hours
  3. temperaturecool to ambient temperature
  4. extractionextract with water
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-007355bcb8584888acf307dd50683d4b
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05932571

Notizen zur Reaktion

Wird geladen…