Potassium Iodide → HCID 57811380, compound

HRID 1037446Notes

Reaction equation

HRID 1037446 reaction equation
Br[C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:10][C:11]1[N:12]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([CH:27]3[CH2:29][CH2:28]3)=[CH:19][CH:18]=2)[C:13]([SH:16])=[N:14][N:15]=1.[I-].[K+]>CN(C=O)C>[NH2:10][C:11]1[N:12]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([CH:27]3[CH2:29][CH2:28]3)=[CH:19][CH:18]=2)[C:13]([S:16][C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:14][N:15]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 178509206HCID 178509206, compound

Product 1

HCID 57811380HCID 57811380, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 2-bromo-2-methylpropanoate (184 μL, 1.239 mmol) was added to a solution of 5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol (0.35 g, 1.239 mmol) in DMF (2.5 mL) and heated at 60° C. for 20 hours after which time a few crystals of potassium iodide were added and the mixture heated at 70° C. for a further 24 h. The temperature was then increased to 90° C. and the mixture heated for an additional 6 days. The mixture was allowed to cool to room temperature, concentrated and dissolved in dichloromethane. Triethylamine and water were added and the layers separated. The aqueous layer was extracted with dichloromethane (2×) and the combined organic extracts dried over NaSO4, filtered, concentrated and purified by column chromatography (ethyl acetate) to afford ethyl 2-(5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)-2-methylpropanoate as a tan solid (0.134 g, 27%).

Workup

  1. additionwere added
  2. temperatureThe temperature was then increased to 90° C.
  3. temperaturethe mixture heated for an additional 6 days
  4. temperatureto cool to room temperature
  5. concentrationconcentrated
  6. dissolutiondissolved in dichloromethane
  7. additionTriethylamine and water were added
  8. customthe layers separated
  9. extractionThe aqueous layer was extracted with dichloromethane (2×)
  10. dry with materialthe combined organic extracts dried over NaSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. custompurified by column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-482700a8ab754c31add3c0636520020a
Source dataset
uspto-grants-2013_10
Patent number
US08546437B2

Reaction notes

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