Trifluoroacetic acid → (S)-1-(6-Fluoro-1-isopropyl-1H-benzoimidazol-2-yl)ethylamine

HRID 243124Notes

Reaction equation

HRID 243124 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH:15]([CH3:17])[CH3:16])[C:13]2[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:22][C:19]1[CH:20]=[CH:21][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([CH:15]([CH3:17])[CH3:16])[C:13]=2[CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68179453[(S)-1-(6-Fluoro-1-isopropyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68157766(S)-1-(6-Fluoro-1-isopropyl-1H-benzoimidazol-2-yl)ethylamineYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(S)-1-(6-Fluoro-1-isopropyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (1.0 g, 3.11 mmol) was dissolved in DCM (10 mL) and TFA (5 mL) added. The reaction mixture was stirred at RT for 30 minutes. The resultant mixture was concentrated in vacuo and the residue dissolved in DCM (40 mL) and stirred vigorously with saturated aqueous NaHCO3 (20 mL), for 10 minutes. The layers were separated and the organic fraction washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound (0.5 g, 72%). 1H NMR (CDCl3, 400 MHz): δ 7.65 (1H, dd, J=8.83, 5.01 Hz), 7.20 (1H, dd, J=9.40, 2.46 Hz), 6.97 (1H, ddd, J=9.58, 8.80, 2.43 Hz), 4.92-4.82 (1H, m), 4.37-4.28 (1H, q, J=6.68 Hz), 1.64 (6H, d, J=6.98 Hz), 1.58 (3H, d, J=6.65 Hz).

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in DCM (40 mL)
  3. stirringstirred vigorously with saturated aqueous NaHCO3 (20 mL), for 10 minutes
  4. customThe layers were separated
  5. washthe organic fraction washed with brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d5a628df1fc4180905366518bb60287
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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