Dimethylformamide → HCID 58981789, compound

HRID 1727930Notes

Reaction equation

HRID 1727930 reaction equation
C1([CH:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:8][CH2:9][O:10][C:11]([C:13]2[C:14]([CH3:30])=[N:15][C:16]([CH3:29])=[C:17](C(O)=O)[C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)=[O:12])C=CC=CC=1.S(Cl)(Cl)=O.[CH3:41][N:42]([CH:44]=[O:45])[CH3:43]>>[C:19]1([CH:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:8][CH2:9][O:10][C:11](=[O:12])[C:13]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)=[C:17]([C:44]([N:42]3[CH2:43][CH2:11][O:10][CH2:9][CH2:41]3)=[O:45])[C:16]([CH3:29])=[N:15][C:14]=2[CH3:30])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 10117784HCID 10117784, compound

Product 1

HCID 58981789HCID 58981789, compound

Procedure

50.0 mg (0.100 mmol) of 4-(3-chlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylic acid mono (3,3-diphenylpropyl) ester and 5 ml of thionyl chloride were stirred in DMF at room temperature for 1 hour. After concentration under reduced pressure, the residue was dissolved in 3 ml of dichloromethane. 1 ml of morpholine was added and stirred at room temperature for 6 hours. After concentration under reduced pressure, ethyl acetate was added and the residue was washed with water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the basic silica gel chromatography (hexane/ethyl acetate=20/1 to 1/4) to obtain the title compound.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. dissolutionthe residue was dissolved in 3 ml of dichloromethane
  3. addition1 ml of morpholine was added
  4. concentrationAfter concentration under reduced pressure, ethyl acetate
  5. additionwas added
  6. washthe residue was washed with water
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by the basic silica gel chromatography (hexane/ethyl acetate=20/1 to 1/4)

Sources & evidence

ORD record
ord-9cae377899cd426aad97f4147661d280
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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