Trifluoroacetic acid → HCID 66754782, compound

HRID 1631987Notes

Reaction equation

HRID 1631987 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([S:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)(=[O:12])=[O:11])[C:8](=[O:21])[N:7]([CH:22]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:23]([N:25]3[CH2:30][CH2:29][N:28]([CH:31]4[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]4)[CH2:27][CH2:26]3)=[O:24])[C:6]=2[CH:50]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([S:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)(=[O:12])=[O:11])[C:8](=[O:21])[N:7]([CH:22]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:23](=[O:24])[N:25]3[CH2:26][CH2:27][N:28]([CH:31]4[CH2:32][CH2:33][NH:34][CH2:35][CH2:36]4)[CH2:29][CH2:30]3)[C:6]=2[CH:50]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66755192HCID 66755192, compound

Product 1

HCID 66754782HCID 66754782, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

122 mg (0.17 mmol) of tert-butyl 4-(4-{2-[6-chloro-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3-dihydrobenzimidazol-1-yl]-2-phenylacetyl}piperazin-1-yl)piperidine-1-carboxylate (Example 127) were dissolved in dichloromethane (3 ml) and while stirring at room temperature, trifluoroacetic acid (3 ml) was added. The reaction solution was stirred for 2 h and then the solvent and excess trifluoroacetic acid were removed in vacuo. The residue was taken up again in toluene, concentrated in vacuo and then dried in vacuo. The residue was dissolved in 15 ml of dichloromethane/methanol (9:1), mixed with 4 eq. of Si-carbonate (Silicycle, 0.69 mmol/g) and stirred at room temperature for 2 h. The solid phase reagent was filtered off and washed with dichloromethane. The filtrate was concentrated under reduced pressure and dried in vacuo. Yield: 105 mg (100%) of colorless oil.

Workup

  1. stirringThe reaction solution was stirred for 2 h
  2. customthe solvent and excess trifluoroacetic acid were removed in vacuo
  3. concentrationconcentrated in vacuo
  4. customdried in vacuo
  5. dissolutionThe residue was dissolved in 15 ml of dichloromethane/methanol (9:1)
  6. stirringstirred at room temperature for 2 h
  7. filtrationThe solid phase reagent was filtered off
  8. washwashed with dichloromethane
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customdried in vacuo

Sources & evidence

ORD record
ord-0db12d01c9d6447b9bf31244ecb79a30
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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