Acetic Acid → HCID 21464388, compound

HRID 1940904Notes

Reaction equation

HRID 1940904 reaction equation
[F:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[N:22]=[C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[C:19](Cl)[N:14]3[N:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([CH3:23])=[CH:4][N:3]=1.C[O-].[Na+].[C:27](O)(=[O:29])C>CS(C)=O.CO.ClCCl>[F:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[N:22]=[C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[C:19]([O:29][CH3:27])[N:14]3[N:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([CH3:23])=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 21464396HCID 21464396, compound

Product 1

HCID 21464388HCID 21464388, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.70 g (1.9 mmol) of N-(2-fluoro-5-methyl-3-pyridinyl)-5-chloro-7-methyl[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide in 25 mL of dry dimethyl sulfoxide was added with stirring 1.0 mL (4.6 mmol) of sodium methoxide as a 25 percent solution in methanol. After 3 min, 3 mL of acetic acid was added and the solution was diluted with 600 mL of dichloromethane. The resulting solution was washed with water (5×100 mL), dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 0.5 g (71 percent of theory) of the title compound as a white solid melting at 262°-264° C. with decomposition.

Workup

  1. washThe resulting solution was washed with water (5×100 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-e5f28bc8a0f6446daf4750be25c0493e
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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