Dimethyl Sulfoxide → N-(5,8-Dimethoxy[1,2,4]triazolo-[1,5-c]pyrimidin 2-yl)-2-methoxy-4-(trifluoromethyl)-3-pyridinesulfonamide

HRID 612829Notes

Reaction equation

HRID 612829 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[N:4]([C:5]([O:13][CH3:14])=[N:6][CH:7]=[C:8]2[O:11][CH3:12])[N:3]=1.[CH3:15][O:16][C:17]1[C:22]([S:23](Cl)(=[O:25])=[O:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=[CH:19][N:18]=1.N1C=CC=CC=1.CS(C)=O>ClCCl.C(#N)C>[CH3:14][O:13][C:5]1[N:4]2[N:3]=[C:2]([NH:1][S:23]([C:22]3[C:17]([O:16][CH3:15])=[N:18][CH:19]=[CH:20][C:21]=3[C:27]([F:30])([F:28])[F:29])(=[O:24])=[O:25])[N:10]=[C:9]2[C:8]([O:11][CH3:12])=[CH:7][N:6]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049Pyridine3×HCID 114468885,8-Dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amineHCID 185397982-Methoxy-4-(trifluoromethyl)pyridine-3-sulfonyl chloride2×

Product 1

HCID 18366179N-(5,8-Dimethoxy[1,2,4]triazolo-[1,5-c]pyrimidin 2-yl)-2-methoxy-4-(trifluoromethyl)-3-pyridinesulfonamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.75 g (93.8 mmol) of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine, 2.1 g (7.6 mmol) of 2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonyl chloride, and 10 mL of dry acetonitrile was prepared and to this was added at ambient temperature with stirring and means to exclude moisture from the system 0.61 mL (7.6 mmol) of dry pyridine, 43 microliters (0.6 mmol) of dry dimethyl sulfoxide, and a small quantity of dry 4A molecular sieves. The mixture was stirred for 5 days. Another 1.0 g (3.4 mmol) of 2-methoxy-4-(trifluoromethyl) pyridine-3-sulfonyl chloride and 0.30 mL (3.5 mmol) of dry pyridine were added and the mixture stirred another 2 days. Another 0.30 mL (3.5 mmol) of dry pyridine was added and stirring continued for 4 more days. The mixture was then diluted with 100 mL of dichloromethane and the resulting mixture was washed with 2×100 mL of 2N aqueous hydrochloric acid, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The tan solid residue was chromatographed on silica gel eluting with a mixture of dichloromethane and ethanol to obtain 0.90 g (54 percent of theory) of the title compound as a white solid melting at 214-216° C.

Workup

  1. customwas prepared
  2. additionto this was added at ambient temperature
  3. dry with materiala small quantity of dry 4A molecular sieves
  4. stirringThe mixture was stirred for 5 days
  5. stirringthe mixture stirred another 2 days
  6. stirringstirring
  7. washthe resulting mixture was washed with 2×100 mL of 2N aqueous hydrochloric acid
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure
  10. customThe tan solid residue was chromatographed on silica gel eluting with a mixture of dichloromethane and ethanol

Sources & evidence

ORD record
ord-38c696f4644f447980f9f89f88f752e4
Source dataset
uspto-grants-1999_12
Patent number
US06005108

Reaction notes

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