Hydrochloric Acid → (S)-1-(6-Fluoro-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamine

HRID 2036568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036568
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([C@@H:11]([NH:13]C(=O)OC(C)(C)C)[CH3:12])[N:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:7]=2[CH:27]=1>O1CCOCC1.C(Cl)Cl>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([C@@H:11]([NH2:13])[CH3:12])[N:8]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:7]=2[CH:27]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 58459376(S)-tert-butyl 1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)ethylcarbamate

Produkt 1

HCID 58459302(S)-1-(6-Fluoro-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

4.0 M HCl in 1,4-dioxane (1.0 mL) was added to a solution of (S)-tert-butyl 1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)ethylcarbamate (12 mg, 0.034 mmol) in DCM (1 mL). After ˜2 h the reaction mixture was concentrated under reduced pressure to dryness. The resulting solid was partitioned between DCM and satd. aq. NaHCO3 solution. The aq. layer was extracted with DCM. The organic layers were combined, dried with Na2SO4, filtered and concentrated under reduced pressure to give (S)-1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)ethanamine: LC-MS (ESI) m/z 256.1 [M+H]+. The product was carried on crude without purification.

Aufarbeitung

  1. concentrationAfter ˜2 h the reaction mixture was concentrated under reduced pressure to dryness
  2. customThe resulting solid was partitioned between DCM
  3. extractionThe aq. layer was extracted with DCM
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0a9e4fe7dfe04d6eb8f4a69efee50e93
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575183B2

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