Trifluoroacetic acid → (S)-1-(6-Fluoro-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamine

HRID 242790Notes

Reaction equation

HRID 242790 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13]2[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:25][C:22]1[CH:23]=[CH:24][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:13]=2[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58459376(S)-tert-butyl 1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)ethylcarbamate

Product 1

HCID 58459302(S)-1-(6-Fluoro-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester (1.20 g, 3.38 mmol) in DCM (5 mL) was added TFA (5 mL) and the resulting mixture was stirred at RT for 1.5 h. The crude reaction mixture was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo affording (S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine as a yellow oil (861 mg, quantitative). LCMS: RT 1.97 and 2.19 min [M+H]+ 256.2

Workup

  1. customThe crude reaction mixture
  2. washThe cartridge was washed with MeOH
  3. washthe product eluted with 2M NH3/MeOH
  4. additionThe product containing fractions
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1793e099c959432fae7c69cbd777c390
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…