Ethyl Acetate → HCID 22180619, compound

HRID 1796763Notes

Reaction equation

HRID 1796763 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].C1([N:13]2[CH2:21][C:20]3[C:15](=[CH:16][C:17]([N:22]4[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH2:30][CH2:31][C:32]5([C:45](=[O:52])[NH:46][CH2:47][C:48]([F:51])([F:50])[F:49])[C:44]6[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=6[C:38]6[C:33]5=[CH:34][CH:35]=[CH:36][CH:37]=6)[CH2:24][CH2:23]4)=CC=3)C2=O)CCCCC1.[C:54](OCC)(=O)[CH3:55]>CN(C=O)C>[F:51][C:48]([F:50])([F:49])[CH2:47][NH:46][C:45]([C:32]1([CH2:31][CH2:30][CH2:29][CH2:28][N:25]2[CH2:24][CH2:23][N:22]([C:17]3[CH:16]=[CH:15][C:20]([C:1]([O:2][CH2:54][CH3:55])=[O:4])=[CH:21][N:13]=3)[CH2:27][CH2:26]2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=2[C:39]2[C:44]1=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:52]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 22180255HCID 22180255, compound

Product 1

HCID 22180619HCID 22180619, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The compound (494 mg, 2.1 mmol) prepared just above in step (b) was dissolved in 8 ml of anhydrous DMF. Potassium carbonate (580 mg) and the compound (892 mg, 2.1 mmol) prepared in step (b) of Example 92 were added to the solution, and the mixture was stirred at 50° C. overnight. The reaction solution was diluted with ethyl acetate, and the dilution was washed twice with water and was then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography (development system, n-hexane:ethyl acetate=1:1) to give ethyl 6-[4-[4-[9-(2,2,2-trifluoroethylcarbamoyl)-9H-fluoren-9-yl]butyl]-piperazin-1-yl]nicotinate (742 mg, yield 62%) as a pale yellow oil.

Workup

  1. washthe dilution was washed twice with water
  2. dry with materialwas then dried 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, n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a97cd8bf673b4fb2b5264f0873bacbf3
Source dataset
uspto-grants-2006_04
Patent number
US07030120B2

Reaction notes

Loading…