Thionyl Chloride → HCID 69518139, compound

HRID 1180016Notes

Reaction equation

HRID 1180016 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]([CH3:32])([CH2:11][C:12](=[O:31])[NH:13][C:14]1[CH:15]=[N:16][C:17]([O:20][C:21](=[O:30])[N:22]([CH3:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:18][CH:19]=1)[CH2:7][C:8]([OH:10])=O.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>ClCCl.CN(C)C=O>[CH3:5][C:6]([CH3:32])([CH2:7][C:8]([N:37]1[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]1)=[O:10])[CH2:11][C:12]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:30])[N:22]([CH3:29])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:16][CH:15]=1)=[O:31]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 531671-MethylpiperazineHCID 22047706HCID 22047706, compound

Product 1

HCID 69518139HCID 69518139, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (56 microL, 0.78 mmol) was added to a stirred solution of 3,3-dimethyl-4-[6-(methyl-phenyl-carbamoyloxy)-pyridin-3-ylcarbamoyl]-butyric acid (0.15 g, 0.39 mmol) in dichloromethane (5 mL) and 2 drops of dimethylformamide. After stirring for 10 minutes N-methylpiperazine (1 mL) was added and stirring was continued for 2 hours. The solvent was evaporated in vacuo. The residue was redissolved in dichloromethane and extracted with water, dried over sodium sulphate, filtered and evaporated in vacuo. The crude product was purified by filtration over a short column (SiO2, ethyl acetate followed by acetone) yielding the title compound (93 mg, 51% yield) as a thick oil.

Workup

  1. additionwas added
  2. customThe solvent was evaporated in vacuo
  3. dissolutionThe residue was redissolved in dichloromethane
  4. extractionextracted with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. filtrationThe crude product was purified by filtration over a short column (SiO2, ethyl acetate followed by acetone)

Sources & evidence

ORD record
ord-559c1e43356c4218908d33c007155cba
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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