Hydrochloric Acid → HCID 57786214, Verbindung

HRID 1399360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399360
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[N:15]([CH2:16][CH2:17][NH:18]C(=O)OC(C)(C)C)[C:14]2[C:26]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[CH:27][CH:28]=[CH:29][C:13]=2[N:12]=1)=O.Cl>CO.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:11]2=[N:12][C:13]3[C:14](=[C:26]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[CH:27]=[CH:28][CH:29]=3)[N:15]2[CH2:16][CH2:17][N:18]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 86632923HCID 86632923, Verbindung

Produkt 1

HCID 57786214HCID 57786214, VerbindungAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of tert-butyl (2-{2-[(2,4-dichlorophenyl)carbonyl]-7-(diethylamino)-1H-benzimidazol-1-yl}ethyl)carbamate (Reference example 224, 395 mg, 0.781 mmol) and hydrochloric acid (10%, methanol solution, 2 mL) in methanol (2 mL) was stirred at room temperature for 14 h and at 50° C. for 2 h. The mixture was diluted with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture to give a yellow amorphous solid (258 mg, 0.666 mmol, 85%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture

Quellen und Nachweise

ORD-Eintrag
ord-04b01da460694158b1a2ef9115c78127
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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