Potassium Carbonate → 2-[(Pyridin-2-yl)methyl]-7-[4-[3-[9-(2,2,2-trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl]piperazin-1-yl]-3,4-dihydro-2H-isoquinolin-1-one

HRID 1796766Notes

Reaction equation

HRID 1796766 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[CH:13][CH:14]=2)[C:9]1=[O:31].C(=O)([O-])[O-].[K+].[K+].[F:38][C:39]([F:62])([F:61])[CH2:40][NH:41][C:42]([C:44]1([CH2:57][CH2:58][CH2:59]Br)[C:56]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[C:50]2[C:45]1=[CH:46][CH:47]=[CH:48][CH:49]=2)=[O:43]>CN(C=O)C.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([N:18]3[CH2:19][CH2:20][N:21]([CH2:59][CH2:58][CH2:57][C:44]4([C:42](=[O:43])[NH:41][CH2:40][C:39]([F:38])([F:61])[F:62])[C:56]5[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=5[C:50]5[C:45]4=[CH:46][CH:47]=[CH:48][CH:49]=5)[CH2:22][CH2:23]3)=[CH:13][CH:14]=2)[C:9]1=[O:31]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 105977593-[9-(2,2,2-Trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl bromideHCID 221804472-[(pyridin-2-yl)methyl]-7-(4-tert-butoxycarbonyl-piperazin-1-yl)-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 221801892-[(Pyridin-2-yl)methyl]-7-[4-[3-[9-(2,2,2-trifluoroethylcarbamoyl)-9H-fluoren-9-yl]propyl]piperazin-1-yl]-3,4-dihydro-2H-isoquinolin-1-oneYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
8 °C

Procedure

The compound (50 mg, 0.16 mmol) prepared in step (b) of Example 125 was dissolved in anhydrous DMF. Potassium carbonate (44 mg) and 66 mg of the compound prepared in step (a) of Example 93 were added to the solution. The mixture was stirred at 50° C. for 20 hr and further at 8° C. for 4.5 hr. The reaction solution was diluted with ethyl acetate, and the dilution was washed twice with water, followed by drying over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography (development system, methylene chloride:methanol=30:1) to give the title compound (46 mg, yield 71%) as a white foam.

Workup

  1. washthe dilution was washed twice with water
  2. dry with materialby drying over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under the reduced pressure
  4. customThe residue was purified by column chromatography (development system, methylene chloride:methanol=30:1)

Sources & evidence

ORD record
ord-284c9d0a1b5447b0a2f312ad9b2557f0
Source dataset
uspto-grants-2006_04
Patent number
US07030120B2

Reaction notes

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