Dimethyl Sulfoxide → N-(4-Bromo-1-methylpyrazol-3-yl)-7-chloro-5-methoxy-1,2,4-triazolo[1,5-c]-pyrimidine-2-sulfonamide

HRID 1645964Notes

Reaction equation

HRID 1645964 reaction equation
N1C=CC=CC=1.CS(C)=O.[Cl:11][C:12]1[N:17]=[C:16]([O:18][CH3:19])[N:15]2[N:20]=[C:21]([S:23](Cl)(=[O:25])=[O:24])[N:22]=[C:14]2[CH:13]=1.[NH2:27][C:28]1[C:32]([Br:33])=[CH:31][N:30]([CH3:34])[N:29]=1>C(#N)C>[Br:33][C:32]1[C:28]([NH:27][S:23]([C:21]2[N:22]=[C:14]3[N:15]([C:16]([O:18][CH3:19])=[N:17][C:12]([Cl:11])=[CH:13]3)[N:20]=2)(=[O:25])=[O:24])=[N:29][N:30]([CH3:34])[CH:31]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 27352834-bromo-1-methyl-1H-pyrazol-3-amineHCID 150036517-Chloro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonyl chloride

Product 1

HCID 19768914N-(4-Bromo-1-methylpyrazol-3-yl)-7-chloro-5-methoxy-1,2,4-triazolo[1,5-c]-pyrimidine-2-sulfonamideYield 25%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyridine (1.08 g, 8 mmol) and dimethyl sulfoxide (0.2 g) were added to a solution of 7-chloro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonyl chloride (1.0 g, 4.0 mmol) and 3-amino-4-bromo-1-methylpyrazole (0.7 g, 4.0 mmol) in 10 mL of acetonitrile with stirring at ambient temperature and the mixture was allowed to react overnight. The mixture was then concentrated by evaporation under reduced pressure and the residue was taken up in methylene chloride. The resulting solution was extracted with water and dried over MgSO4. The volatile materials were then removed by evaporation under reduced pressure and the solid residue was extracted with diethyl ether and with water, recovered by filtration, and dried under reduced pressure to obtain 0.38 g (25 percent yield) of the title compound as a white solid melting at 230°-232° C.

Workup

  1. customto react overnight
  2. concentrationThe mixture was then concentrated by evaporation under reduced pressure
  3. extractionThe resulting solution was extracted with water
  4. dry with materialdried over MgSO4
  5. customThe volatile materials were then removed by evaporation under reduced pressure
  6. extractionthe solid residue was extracted with diethyl ether and with water
  7. filtrationrecovered by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-ec4798ddd9b9472680f8a946022a9d8d
Source dataset
uspto-grants-1993_01
Patent number
US05177206

Reaction notes

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