Trifluoroacetic acid → (S)-1-(7-Bromo-6-fluoro-1-methyl-1H-benzoimidazol-2-yl)ethylamine

HRID 243187Notes

Reaction equation

HRID 243187 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C@H:15]([C:17]1[N:21]([CH3:22])[C:20]2[C:23]([Br:28])=[C:24]([F:27])[CH:25]=[CH:26][C:19]=2[N:18]=1)[CH3:16])(C)(C)C>C(Cl)Cl>[Br:28][C:23]1[C:20]2[N:21]([CH3:22])[C:17]([C@@H:15]([NH2:14])[CH3:16])=[N:18][C:19]=2[CH:26]=[CH:25][C:24]=1[F:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157629[(S)-1-(7-bromo-6-fluoro-1-methyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68157037(S)-1-(7-Bromo-6-fluoro-1-methyl-1H-benzoimidazol-2-yl)ethylamineYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (40 mL) was added to a solution of [(S)-1-(7-bromo-6-fluoro-1-methyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (3.02 g, 8.11 mmol) in DCM (20 mL) and stirred for 15 minutes. The reaction mixture was concentrated in vacuo and the residue partitioned between DCM and saturated aqueous NaHCO3. The combined DCM extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound as a white solid (2.04 g, 92%). LCMS (Method C): RT 1.83 min [M+H]+ 271.9, 273.9

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between DCM and saturated aqueous NaHCO3
  3. dry with materialThe combined DCM extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f09ca89c1df41dc861603a4c9b75181
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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