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

HRID 242900Notes

Reaction equation

HRID 242900 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:11]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:13]=2[N:12]=1)[CH2:9][CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:26][C:23]1[CH:24]=[CH:25][C:13]2[N:12]=[C:11]([C@@H:8]([NH2:7])[CH2:9][CH3:10])[N:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:14]=2[CH:22]=1

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)propyl]carbamic acid tert-butyl ester (234 mg, 0.63 mmol) in DCM (3 mL) was added TFA (1.5 mL) and the mixture stirred at RT for 2 h. The volatiles were removed in vacuo and the resulting residue partitioned between DCM (20 mL) and a saturated aqueous solution of NaHCO3. The two phase system was stirred for 10 min, then the organic fraction dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford the title compound as a colourless oil (42 mg, 25%). LCMS (Method B): RT 1.90 min [M−NH2]+ 253.0.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue partitioned between DCM (20 mL)
  3. stirringThe two phase system was stirred for 10 min
  4. dry with materialthe organic fraction 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-8413817172844815806aaead5001f251
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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