Trifluoroacetic acid → (S)-1-(7-Fluoro-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamine

HRID 242786Notes

Reaction equation

HRID 242786 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[C:21]([F:25])=[CH:22][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:21]1[C:13]2[N:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:10]([C@@H:8]([NH2:7])[CH3:9])=[N:11][C:12]=2[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157602[(S)-1-(7-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester

Product 1

HCID 68157214(S)-1-(7-Fluoro-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamineYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(7-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester (625 mg) in DCM (3 mL) was added TFA (3 mL) and the resulting mixture was stirred at RT for 3 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-(7-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine as a pale orange oil (372 mg, 83%). LCMS: RT 1.97 and 2.11 min [M+H]+ 255.9.

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-872b8c15a7ce401d9ce3842897fc6af4
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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