HCID 9905207, compound → HCID 9800766, compound

HRID 1244996Notes

Reaction equation

HRID 1244996 reaction equation
C(O[CH2:5][CH2:6][N+:7]([O-:9])=[O:8])(=O)C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:21]=[CH:20][N:19]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[C:18]=2[C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:13][CH:12]=1>C(O)C>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:21]=[CH:20][N:19]([CH:22]3[CH2:23][CH2:24][N:25]([CH2:5][CH2:6][N+:7]([O-:9])=[O:8])[CH2:26][CH2:27]3)[C:18]=2[C:28]2[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 9905207HCID 9905207, compoundHCID 118153992-nitroethyl Acetate

Product 1

HCID 9800766HCID 9800766, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

186 mg (1.40 mmol) of 2-nitroethyl acetate were added to a solution of 300 mg (0.93 mmol) of 3-(4-fluorophenyl)-1-(piperidin-4-yl)-2-(pyridin-4-yl)-1H-pyrrole (prepared as described in Example 13 above) in 6 ml of ethanol. The resulting mixture was stirred at room temperature for 30 minutes, after which the solvent was distilled off under reduced pressure. A saturated aqueous solution of sodium hydrogencarbonate was added to the residue and then this was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The residual solid was washed with diethylether to give 280 mg (yield 76%) of the title compound as a white powder.

Workup

  1. distillationafter which the solvent was distilled off under reduced pressure
  2. additionA saturated aqueous solution of sodium hydrogencarbonate was added to the residue
  3. extractionthis was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. washThe residual solid was washed with diethylether

Sources & evidence

ORD record
ord-909e67c61b8544c0a30d128c8a6f5035
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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