Trifluoroacetic acid → (S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)propylamine

HRID 242865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 242865
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH:13]C(=O)OC(C)(C)C)[CH2:11][CH3:12])[N:7]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:6]=2[CH:27]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH2:13])[CH2:11][CH3:12])[N:7]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:6]=2[CH:27]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 68158046(S)-tert-butyl 1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)propylcarbamate

Produkt 1

HCID 68157917(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)propylamineAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-tert-butyl 1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)propylcarbamate (234 mg, 0.63 mmol) in DCM (3 mL) was added TFA (1.5 mL) and the mixture was stirred at RT for 2 h. Volatiles were removed under reduced pressure and the resulting residue was partitioned between DCM (20 mL) and a saturated solution of NaHCO3. The two phase system was stirred for 10 min, then the organic layer was dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) affording (S)-1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)propan-1-amine as a colourless oil (42 mg, 25%). LCMS: RT 1.90 min [M−NH2] 253.0

Aufarbeitung

  1. customVolatiles were removed under reduced pressure
  2. customthe resulting residue was partitioned between DCM (20 mL)
  3. stirringThe two phase system was stirred for 10 min
  4. dry with materialthe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-feb13c645ac34f978b06c17c791dad6f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

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