Piperidine → HCID 17854627, compound

HRID 1727887Notes

Reaction equation

HRID 1727887 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:15])=[C:12]([CH3:26])[N:11]=[C:10](SC)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.ClC1C=CC=C(C(OO)=O)C=1.S(=O)(O)[O-].[Na+].[NH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:15])=[C:12]([CH3:26])[N:11]=[C:10]([N:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 70297m-Chloroperbenzoic acidHCID 17854639HCID 17854639, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 17854627HCID 17854627, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

44.0 mg (0.107 mmol) of 4-(3-chlorophenyl)-6-methyl-2-(methylthio)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide was dissolved in 5 ml of dichloromethane. 36.9 mg (0.213 mmol) of mCPBA (m-chloroperbenzoic acid) was added thereto at 0° C. and stirred at the same temperature for 6 hours. 1 ml of saturated aqueous sodium bisulfite solution was added thereto at the same temperature and stirred for 30 minutes heating to room temperature. After the reaction mixture was diluted with dichloromethane, the organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was dissolved in 5 ml of toluene and 91.1 mg (1.07 mmol) of piperidine was added at room temperature and stirred at 80° C. for 6 hours. After concentration under reduced pressure, the obtained residue was diluted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography hexane/ethyl acetate=10/1 to 1/1) to obtain the title compound.

Workup

  1. stirringat the same temperature and stirred for 30 minutes
  2. temperatureheating to room temperature
  3. washthe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe obtained residue was dissolved in 5 ml of toluene
  7. stirringstirred at 80° C. for 6 hours
  8. concentrationAfter concentration under reduced pressure
  9. additionthe obtained residue was diluted with ethyl acetate
  10. washThe organic layer was washed with saturated aqueous sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by the silica gel chromatography hexane/ethyl acetate=10/1 to 1/1)

Sources & evidence

ORD record
ord-169a3a6db2174fc7ba5b9e48e8f50f47
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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