Acetic Acid → HCID 19080735, compound

HRID 963165Notes

Reaction equation

HRID 963165 reaction equation
C[O-].[Na+].CO.[CH2:6]([N:8]1[C:12]([CH3:13])=[C:11]([NH:14][S:15]([C:18]2[N:28]=[C:21]3[CH:22]=[C:23]([CH3:27])[CH:24]=[C:25](Cl)[N:20]3[N:19]=2)(=[O:17])=[O:16])[C:10]([C:29]([F:32])([F:31])[F:30])=[N:9]1)[CH3:7].[C:33](O)(=[O:35])C>CS(C)=O>[CH2:6]([N:8]1[C:12]([CH3:13])=[C:11]([NH:14][S:15]([C:18]2[N:28]=[C:21]3[CH:22]=[C:23]([CH3:27])[CH:24]=[C:25]([O:35][CH3:33])[N:20]3[N:19]=2)(=[O:17])=[O:16])[C:10]([C:29]([F:32])([F:31])[F:30])=[N:9]1)[CH3:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 19080766HCID 19080766, compound

Product 1

HCID 19080735HCID 19080735, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 25 percent solution of sodium methoxide in methanol (1.65 g, 5.4 mmol) was added to a solution of 1.14 g (2.70 mmol) of N-(1-ethyl-5-methyl-3-(trifluoromethyl)-4-pyrazolyl)-5-chloro-7-methyl[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide in 25 mL of dimethyl sulfoxide (DMSO) at ambient temperature with stirring. After 18 hours, 1.0 mL of acetic acid was added and the resulting mixture was concentrated by evaporation under reduced pressure. The residue was diluted with 25 mL of water and the resulting slurry was stirred for 10 min and then the insoluble solids collected by filtration, washed twice with 10 mL portions of water and then with 25 mL of ether, and dried under reduced pressure at 40° C. overnight. The resulting white solid, which amounted to 1.03 g (92 percent of theory) and melted at 230°-231° C. (d), was the title compound (Compound 2).

Workup

  1. concentrationthe resulting mixture was concentrated by evaporation under reduced pressure
  2. additionThe residue was diluted with 25 mL of water
  3. stirringthe resulting slurry was stirred for 10 min
  4. filtrationthe insoluble solids collected by filtration
  5. washwashed twice with 10 mL portions of water
  6. dry with materialwith 25 mL of ether, and dried under reduced pressure at 40° C. overnight

Sources & evidence

ORD record
ord-a65dbfb3a46146729f0f63949949ec2e
Source dataset
uspto-grants-1998_06
Patent number
US05763359

Reaction notes

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