Water → HCID 57597979, compound

HRID 1886822Notes

Reaction equation

HRID 1886822 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH:12]=2)=[CH:7][C:4]=1[C:5]#[N:6].[OH-].[Na+].O>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[CH:7][C:4]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 57597867HCID 57597867, compound

Product 1

HCID 57597979HCID 57597979, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The nitrile 37 (95.8 mg, 237 μmol) was dissolved in dioxane (5 ml) and treated with 2N sodium hydroxide in water (250 μl, 500 μmol). The reaction was sealed and heated to reflux for 2 hours. The reaction was concentrated to dryness and extracted with ethyl acetate and water. The organics were washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product (72.3 mg). The crude was purified via flash chromatography and eluted with a gradient from 1:1 ethyl acetate/hexane to 100% ethyl acetate to 4/4/1 ethyl acetate/hexane/7N ammonia in methanol to give 38 (26.7 mg, 45%).

Workup

  1. customThe reaction was sealed
  2. temperatureheated
  3. temperatureto reflux for 2 hours
  4. concentrationThe reaction was concentrated to dryness
  5. extractionextracted with ethyl acetate and water
  6. washThe organics were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give crude product (72.3 mg)
  11. customThe crude was purified via flash chromatography
  12. washeluted with a gradient from 1:1 ethyl acetate/hexane to 100% ethyl acetate to 4/4/1 ethyl acetate/hexane/7N ammonia in methanol

Sources & evidence

ORD record
ord-e5cdf34df10c43e8927b0c18092ecdd0
Source dataset
uspto-grants-2013_08
Patent number
US08501446B2

Reaction notes

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