Trifluoroacetic acid → HCID 14685682, compound

HRID 1380056Notes

Reaction equation

HRID 1380056 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([N:17]=[C:18]([NH:20][C:21](=[O:23])[CH3:22])[N:19]=2)[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)=[N:6][CH:7]=1.FC(F)(F)C(O)=O.[H][H]>[Pd].C(=O)([O-])[O-].[K+].[K+]>[NH2:14][C:10]1[CH:9]=[C:8]([C:5]2[N:4]3[N:17]=[C:18]([NH:20][C:21](=[O:23])[CH3:22])[N:19]=[C:3]3[C:2]([CH3:1])=[CH:7][N:6]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 13590348HCID 13590348, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14685682HCID 14685682, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 11430Potassium CarbonateSolvent

Procedure

A 5.0 g portion of N-[8-methyl-5-(3-nitrophenyl)[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]acetamide in a solution of 20 ml of trifluoroacetic acid containing 500 mg of 10% palladium on carbon catalyst was shaken under 46 lb. of hydrogen pressure on a Paar hydrogenator overnight. The mixture was filtered and the filtrate evaporated, giving an oil. This oil was neutralized with 20 ml of saturated aqueous potassium carbonate, saturated with salt and extracted into 100 ml of ethyl acetate. The organic phase was dried, filtered and evaporated. The residue was recrystallized from ethanol, giving 3.4 g of N-[5-(3-aminophenyl)-8-methyl[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]acetamide. A 282 mg portion of the above compound and 210 mg of p-toluene sulfonyl chloride were dissolved in 100 ml of pyridine with stirring and sealed overnight. A 105 mg portion of p-toluene sulfonyl chloride was added and the mixture was warmed under a drying tube on a steam bath for 1/2 hour. The mixture was cooled, evaporated and the residue taken up in chloroform and passed through a hydrous magnesium silicate pad. The filtrate was taken up in chloroform, washed with 0.1N hydrochloric acid, dried and evaporated. This residue was recrystallized from ethyl acetate-cyclohexane, giving the desired product as white crystals, mp 215°-218° C.

Workup

  1. customon a Paar hydrogenator overnight
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated
  4. customgiving an oil
  5. extractionextracted into 100 ml of ethyl acetate
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-22750f7977014071b363e039f99dded3
Source dataset
uspto-grants-1986_04
Patent number
US04579848

Reaction notes

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