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

HRID 243182Notes

Reaction equation

HRID 243182 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C@H:15]([C:18]1[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:21]2[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:20]=2[N:19]=1)[CH2:16][CH3:17])(C)(C)C>C(Cl)Cl>[F:33][C:30]1[CH:31]=[CH:32][C:20]2[N:19]=[C:18]([C@@H:15]([NH2:14])[CH2:16][CH3:17])[N:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:21]=2[CH:29]=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 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.50 mL, 6.73 mmol) was added to a solution of [(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)propyl]carbamic acid tert-butyl ester (92 mg, 0.25 mmol) in DCM (2 mL) and the reaction stirred at RT for 1.5 h. The reaction mixture was concentrated in vacuo and passed through a 2 g Isolute® SCX-2 cartridge, eluting with 2M NH3/MeOH. The basic fraction was concentrated in vacuo to give the title compound (57 mg, 85%) as a red oil. LCMS (Method J): RT=2.08 min, [M+H]+=270.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washeluting with 2M NH3/MeOH
  3. concentrationThe basic fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-c6d32b46478a43b1b3b58e9f03d2d332
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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