Sodium Iodide → N-(1-Methylpyrazol-3-yl)-7-chloro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamide

HRID 1589999Notes

Reaction equation

HRID 1589999 reaction equation
[I-].[Na+].C[Si](Cl)(C)C.[NH2:8][C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[N:10]=1.C(N(CC)CC)C.[Cl:22][C:23]1[N:28]=[C:27]([O:29][CH3:30])[N:26]2[N:31]=[C:32]([S:34](Cl)(=[O:36])=[O:35])[N:33]=[C:25]2[CH:24]=1>C(#N)C.CS(C)=O>[CH3:14][N:11]1[CH:12]=[CH:13][C:9]([NH:8][S:34]([C:32]2[N:33]=[C:25]3[N:26]([C:27]([O:29][CH3:30])=[N:28][C:23]([Cl:22])=[CH:24]3)[N:31]=2)(=[O:35])=[O:36])=[N:10]1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 1372541-Methyl-3-aminopyrazole2×HCID 150036517-Chloro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonyl chloride

Product 1

HCID 19768918N-(1-Methylpyrazol-3-yl)-7-chloro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideCatalystHCID 6342AcetonitrileSolvent

Procedure

Sodium iodide (3.6 g, 24 mmol) and trimethylsilyl chloride 92.6 g, 24 mmol) were added to a solution of 3-amino-1-methylpyrazole (2.3 g, 24 mmol) and triethylamine (2.5 g, 25 mmol) in 20 mL of acetonitrile at ambient temperature with stirring and under dry nitrogen. The mixture was allowed to react until the 3-amino-1-methylpyrazole was essentially all consumed as determined by gas-liquid chromatography. The solvent was then removed by evaporation under reduced pressure and the residue was taken up in diethyl ether. The resulting mixture was filtered to remove solids and the ether was removed by evaporation under reduced pressure. The residue was dissolved in 10 mL of acetonitrile and the resulting solution was combined with 7-chloro-5-methoxy-1,2,4-triazolo[1,5-c]-pyrimidine-2-sulfonyl chloride (2.0 g, 7.0 mmol) and to this was added with stirring at ambient temperature about 0.2 mL of dimethyl sulfoxide catalyst. The resulting mixture was allowed to react for 24 hours and was then concentrated under reduced pressure and the residue was diluted with first water and then methylene chloride. The organic layer was recovered, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure to obtain the title compound as a white solid, which, after drying, amounted to 2.4 g (98 percent of theory) and melted at 185°-187° C.

Workup

  1. customall consumed
  2. customThe solvent was then removed by evaporation under reduced pressure
  3. filtrationThe resulting mixture was filtered
  4. customto remove solids
  5. customthe ether was removed by evaporation under reduced pressure
  6. dissolutionThe residue was dissolved in 10 mL of acetonitrile
  7. additionto this was added
  8. customto react for 24 hours
  9. concentrationwas then concentrated under reduced pressure
  10. additionthe residue was diluted with first water
  11. customThe organic layer was recovered
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b2a8d44123184085935fd5dcf78d3ee1
Source dataset
uspto-grants-1993_04
Patent number
US05201938

Reaction notes

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