Trifluoroacetic acid → HCID 66754850, compound

HRID 1643972Notes

Reaction equation

HRID 1643972 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:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:23]([NH:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]3)=[O:24])[C:6]=2[CH:47]=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:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)(=[O:11])=[O:12])[C:8](=[O:21])[N:7]([CH:22]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:23]([NH:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]3)=[O:24])[C:6]=2[CH:47]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66755367HCID 66755367, compound

Product 1

HCID 66754850HCID 66754850, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

520 (0.76 mmol) of tert-butyl 4-(2-{2-[6-chloro-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3-dihydrobenzimidazol-1-yl]-2-phenyl-acetylamino}-ethyl)piperazine-1-carboxylate (Example 130) were dissolved in dichlormethane (6 ml) and, while stirring at room temperature, trifluoroacetic acid (4 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 once again in toluene, concentrated in vacuo and then dried in vacuo. The residue was dissolved in 6 ml of dichloromethane, mixed with 3 eq. of MP carbonate (Argonaut, 1.69 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: 430 mg (97%) 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 6 ml of dichloromethane
  6. additionmixed with 3 eq. of MP carbonate (Argonaut, 1.69 mmol/g)
  7. stirringstirred at room temperature for 2 h
  8. filtrationThe solid phase reagent was filtered off
  9. washwashed with dichloromethane
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customdried in vacuo

Sources & evidence

ORD record
ord-c68fef6cd45b44759ddb8bd19f05806a
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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