Dimethyl Sulfoxide → HCID 69901548, compound

HRID 2308008Notes

Reaction equation

HRID 2308008 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]1[C:9]([NH:10][CH:11]([CH2:14]OS(C)(=O)=O)[CH2:12][CH3:13])=[CH:8][C:7]([CH3:20])=[N:6][C:5]=1[O:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([O:29][CH3:30])=[CH:24][C:23]=1[CH3:31].[I-].[Na+].[CH3:35][S:36](C)=O>C(#N)C>[CH3:1][O:2][C:3](=[O:32])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][S:36][CH3:35])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:20])=[N:6][C:5]=1[O:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([O:29][CH3:30])=[CH:24][C:23]=1[CH3:31]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5238Sodium IodideHCID 86584331HCID 86584331, compound

Product 1

HCID 69901548HCID 69901548, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(4-methoxy-2,6-dimethyl-phenoxy)-4-(1-methanesulfonyloxymethyl-propylamino)-6-methyl-nicotinic acid methyl ester and sodium iodide in acetonitrile was stirred at rt for 2 hr, then NaSMe was added. The mixture was heated at 60° C. overnight. DMSO and additional NaSMe were added and heated for additional hours until all starting material was consumed. The mixture was quenched with water, extracted with ethyl acetate. The organic layer was separated, dried, concentrated, and purified to give the title compound.

Workup

  1. additionNaSMe was added
  2. temperatureThe mixture was heated at 60° C. overnight
  3. temperatureheated for additional hours until all starting material
  4. customwas consumed
  5. customThe mixture was quenched with water
  6. extractionextracted with ethyl acetate
  7. customThe organic layer was separated
  8. customdried
  9. concentrationconcentrated
  10. custompurified

Sources & evidence

ORD record
ord-01e3e26fe5204b5e92e404f36714de2c
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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