Pyridine → HCID 69517859, compound

HRID 1831391Notes

Reaction equation

HRID 1831391 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]([CH3:31])([CH2:10][C:11]([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)=[O:12])[C:7](O)=[O:8].N1C=CC=CC=1>ClCCl>[CH3:5][C:6]1([CH3:31])[CH2:10][C:11](=[O:12])[N:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:30])[N:22]([CH3:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:16][CH:15]=2)[C:7]1=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 22047738HCID 22047738, compound

Product 1

HCID 69517859HCID 69517859, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of thionyl chloride (0.726 mL, 10.00 mmol) and 2,2-dimethyl-N-[6-(methyl-phenyl-carbamoyloxy)-pyridin-3-yl]-succinamic acid (0.74 g, 2.00 mmol) in dichloromethane (25 mL) was stirred at room temperature for 18 hours. The solvent and excess thionyl chloride were evaporated in vacuo. The crude product was redissolved in dichloromethane (25 mL) and pyridine (316 mg, 4.00 mmol) was added. The solution was extracted with water, dried over sodium sulphate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50), yielding the title compound (490 mg, 69% yield) as a white solid.

Workup

  1. customThe solvent and excess thionyl chloride were evaporated in vacuo
  2. dissolutionThe crude product was redissolved in dichloromethane (25 mL)
  3. extractionThe solution was extracted with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50)

Sources & evidence

ORD record
ord-be85a8f6816248bc963aa5fea7b57223
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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