HCID 136353921, compound → HCID 135823072, compound

HRID 2243222Notes

Reaction equation

HRID 2243222 reaction equation
[CH3:1][C:2]1[NH:6][C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:16]=[C:17]([C:21]4([C:27]([NH:29][CH2:30][C:31]#[CH:32])=[O:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:18]=[CH:19][CH:20]=3)=[CH:10][CH:9]=2)[N:3]=1>C(O)(=O)C>[CH3:1][C:2]1[NH:6][C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]4([C:27]5[O:28][C:31]([CH3:32])=[CH:30][N:29]=5)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[CH:16]=3)=[CH:10][CH:9]=2)[N:3]=1

Participants

3

Reactant 1

HCID 136353921HCID 136353921, compound

Product 1

HCID 135823072HCID 135823072, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-(3-{[4-(3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phenyl]thio}phenyl)-N-prop-2-yn-1-yltetrahydro-2H-pyran-4-carboxamide (1.0 mmol) (example 16) and mercuric acetate (0.11 mmol) in acetic acid is heated at reflux for about 3 hours. All the volatiles are removed under reduced pressure and an aqueous solution of saturated potassium carbonate is added to the residue. The mixture is then extracted with dichloromethane, and the organic layer is dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The residue is then purified by column chromatography over silica gel to yield the title compound.

Workup

  1. temperatureat reflux for about 3 hours
  2. customAll the volatiles are removed under reduced pressure
  3. additionan aqueous solution of saturated potassium carbonate is added to the residue
  4. extractionThe mixture is then extracted with dichloromethane
  5. dry with materialthe organic layer is dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is then purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-f6ba517a1484497ba9f413bc852748a2
Source dataset
uspto-grants-2010_03
Patent number
US07674811B2

Reaction notes

Loading…