Trifluoroacetic acid → 3-(3,5-Difluorophenyl)-6-(3-(piperazin-1-yl)propoxy)-2-(quinolin-3-yl)-1H-inden-1-one

HRID 331355Notes

Reaction equation

HRID 331355 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)=[CH:15][CH:16]=3)[C:11](=[O:35])[C:10]=2[C:36]2[CH:37]=[N:38][C:39]3[C:44]([CH:45]=2)=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:5]=[C:6]([F:8])[CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]4)=[CH:15][CH:16]=3)[C:11](=[O:35])[C:10]=2[C:36]2[CH:37]=[N:38][C:39]3[C:44]([CH:45]=2)=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70310450t-Butyl 4-(3-(3-(3,5-difluorophenyl)-1-oxo-2-(quinolin-3-yl)-1H-inden-6-yloxy)propyl)piperazine-1-carboxylate

Product 1

HCID 703128333-(3,5-Difluorophenyl)-6-(3-(piperazin-1-yl)propoxy)-2-(quinolin-3-yl)-1H-inden-1-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of tert-butyl 4-(3-(3-(3,5-difluorophenyl)-1-oxo-2-(quinolin-3-yl)-1H-inden-6-yloxy)propyl)piperazine-1-carboxylate (42 mg, 0.1 mmol) obtained in Step 2 in CH2Cl2 was added trifluoroacetic acid (20 eq, 1.0 mmol). After being stirred for 1 h, the mixture was diluted with CH2Cl2 and basicified to pH 9 with a 3N NaOH solution. The organic layer was washed with H2O and brine, dried over MgSO4, and concentrated in vacuo to provide the title compound, which was used in the next step without further purification.

Workup

  1. washThe organic layer was washed with H2O and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96d2ba4edc9f43a6b3714581212251a0
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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