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

HRID 331316Notes

Reaction equation

HRID 331316 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][CH:39]=[CH:40][CH:41]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[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][NH:25][CH2:24][CH2:23]4)=[CH:15][CH:16]=3)[C:11](=[O:35])[C:10]=2[C:36]2[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 51001940tert-butyl 4-(3-(3-(3,5-difluorophenyl)-1-oxo-2-(pyridin-3-yl)-1H-inden-6-yloxy)propyl)piperazine-1-carboxylate

Product 1

HCID 510019386-(3-(piperazin-1-yl)propoxy)-3-(3,5-difluorophenyl)-2-(pyridin-3-yl)-1H-inden-1-oneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 10 mL round-bottomed flask, tert-butyl 4-(3-(3-(3,5-difluorophenyl)-1-oxo-2-(pyridin-3-yl)-1H-inden-6-yloxy)propyl)piperazine-1-carboxylate (107.5 mg, 0.19 mmol) obtained in Step 2 of Example 64 and CH2Cl2 (2 mL, 0.1M) were charged. Trifluoroacetic acid (0.6 mL, 40.0 eq) was added dropwise over 5 min at 0° C. After being stirred for 2 h, the mixture was quenched with H2O and washed with CH2Cl2. The aqueous layer was basicified to pH 9 with a 15% NaOH solution and extracted with CH2Cl2. The extracts were concentrated in vacuo to provide the title compound (80 mg, 93%).

Workup

  1. customthe mixture was quenched with H2O
  2. washwashed with CH2Cl2
  3. extractionextracted with CH2Cl2
  4. concentrationThe extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-6d3843bedeb34333abc7513c9d7774b3
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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