Trifluoroacetic acid → HCID 68157212, compound

HRID 242868Notes

Reaction equation

HRID 242868 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:7]([C@@H:9]([NH:11]C(=O)OC(C)(C)C)[CH3:10])=[N:8][C:4]=2[CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:7]([C@@H:9]([NH2:11])[CH3:10])=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58459222HCID 58459222, compound

Product 1

HCID 68157212HCID 68157212, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-(5-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)ethylcarbamate (661 mg, 1.9 mmol) in DCM (9 mL) was added TFA (4.5 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 (40 mL). 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-(5-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)ethanamine as a yellow oil (379 mg, 78%). LCMS: RT 1.77 min [M+H]+ 256.2

Workup

  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)

Sources & evidence

ORD record
ord-cea6c9135c484f4396d9bb0eb92ecb97
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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