Trifluoroacetic acid → HCID 178464790, compound

HRID 2053773Notes

Reaction equation

HRID 2053773 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]2[NH:6][C:7]([CH:9]([NH:11][C:12](=[O:36])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([N:21]4[CH2:25][CH2:24][CH2:23][CH:22]4[CH2:26][NH:27]C(OC(C)(C)C)=O)=[O:20])=[C:15]([Cl:35])[CH:14]=3)[CH3:10])=[N:8][C:4]=2[CH:3]=1.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:38]=[CH:37][C:5]2[NH:6][C:7]([CH:9]([NH:11][C:12](=[O:36])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([N:21]4[CH2:25][CH2:24][CH2:23][CH:22]4[CH2:26][NH2:27])=[O:20])=[C:15]([Cl:35])[CH:14]=3)[CH3:10])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178464791HCID 178464791, compound

Product 1

HCID 178464790HCID 178464790, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.25 g (0.446 mmol) of N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-3-chloro-4-[2-(N-tert-butoxycarbonylaminomethyl)pyrrolidin-1-ylcarbonyl]benzamide (Example 9) is dissolved in 10 mL of dichloromethane and after the addition of 0.68 mL (8.9 mmol) of trifluoroacetic acid stirred for 1 hour at ambient temperature. After elimination of the volatile constituents in vacuo, the residue is taken up in ethyl acetate, the solution washed twice with 2 molar sodium hydroxide solution and three times with demineralized water, and dried over sodium sulfate. Finally, the solvent is eliminated in vacuo. Yield: 120 mg (58%; mixture of all four stereoisomers); Rf value: 0.10 (silica gel; dichloromethane/ethanol=9:1); C22H23Cl2N5O2 (460.36); mass spectrum: (M+H)+=460/462/464 (chlorine isotope).

Workup

  1. washthe solution washed twice with 2 molar sodium hydroxide solution and three times with demineralized water
  2. dry with materialdried over sodium sulfate
  3. additionmixture of all four stereoisomers)

Sources & evidence

ORD record
ord-6f131bd50e5f447a89989fa4c8cd2595
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…