Trifluoroacetic acid → HCID 68157869, compound

HRID 242912Notes

Reaction equation

HRID 242912 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]([Cl: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>[Cl: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 68157782HCID 68157782, compound

Product 1

HCID 68157869HCID 68157869, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(6-chloro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (1.20 g, 3.23 mmol) in DCM (5 mL) was added TFA (5 mL) and the mixture stirred at RT for 3 h. The crude mixture was loaded into an Isolute® SCX-2 cartridge then washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo to afford (S)-1-(6-chloro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine as a yellow oil (796 mg, 91%).

Workup

  1. washthen washed with MeOH
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a7d28dab9e54fa585ef592f8a2b8286
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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