Trifluoroacetic acid → (S)-1-(1-Benzyl-6-fluoro-1H-benzoimidazol-2-yl)ethylamine

HRID 243120Notes

Reaction equation

HRID 243120 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH3:7].[CH2:15]([N:14]1[C:13]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:12]=2[N:11]=[C:10]1[C@@H:8]([NH2:7])[CH3:9])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68179451[(S)-1-(1-Benzyl-6-fluoro-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester

Product 2

HCID 222AmmoniaHCID 68157972(S)-1-(1-Benzyl-6-fluoro-1H-benzoimidazol-2-yl)ethylamineYield 186.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(S)-1-(1-Benzyl-6-fluoro-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (0.88 g, 2.39 mmol) was dissolved in DCM (10 mL) and TFA (4 mL) was added dropwise. The pale green mixture was stirred at RT for 1 h, under an atmosphere of nitrogen. The resultant mixture was concentrated in vacuo and the residue passed down an Isolute® SCX-2 cartridge, eluting with DCM, MeOH and then 2M NH3 in MeOH solution to afford the title compound as a pale red gum (0.60 g, 93%). 1H NMR (CDCl3, 400 MHz): δ 7.69 (1H, dd, J=8.81, 4.80 Hz), 7.37-7.28 (3H, m), 7.09-7.95 (3H, m), 6.89 (1H, dd, J=8.75, 2.44 Hz), 5.54-5.34 (2H, m), 4.26 (1H, q, J=6.67 Hz), 1.54 (3H, d, J=6.61 Hz)

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. washeluting with DCM, MeOH

Sources & evidence

ORD record
ord-f5709fa407b747b4a6d4fccab06e071f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…