p-Toluenesulfonic acid → HCID 20161352, compound

HRID 247042Notes

Reaction equation

HRID 247042 reaction equation
[CH2:1]([N:5]1[CH2:9][C:8](=O)[CH:7](C(OCC)=O)[C:6]1=[O:16])[CH2:2][CH2:3][CH3:4].[NH2:17][C:18]1[N:22]([CH2:23][CH2:24][C:25]#[C:26][CH3:27])[N:21]=[CH:20][C:19]=1[C:28]#[N:29].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C.C1(C)C=CC=CC=1>[NH2:29][C:28]1[C:7]2[C:6](=[O:16])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:9][C:8]=2[N:17]=[C:18]2[N:22]([CH2:23][CH2:24][C:25]#[C:26][CH3:27])[N:21]=[CH:20][C:19]=12

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 15190748HCID 15190748, compoundHCID 20161353HCID 20161353, compound

Product 1

HCID 20161352HCID 20161352, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(n-butyl)-3-ethoxycarbonyl-pyrrolidin-2,4-dione (1.02 g.) in wet acetonitrile (23 ml.) was heated under reflux for 1.5 hours. The acetonitrile was evaporated under reduced pressure, leaving a clear oil which was immediately dissolved in toluene (28 ml.). To this solution was added 5-amino-1-(pent-3-ynyl)-4-cyanopyrazole (0.6 g.) and a catalytic amount of toluene-p-sulphonic acid (0.05 g.). The mixture was heated under reflux overnight, collecting water in a Dean-Stark trap. The reaction mixture was cooled to 0° and diluted with ether. The resulting precipitate was collected by filtration, giving 0.89 g. of 5-[N-(n-butyl)-2-oxo-3-pyrrolin-4-yl]amino-1-(pent-3-ynyl)-4-cyanopyrazole, which was used without further purification.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. customThe acetonitrile was evaporated under reduced pressure
  3. customleaving a clear oil which
  4. temperatureThe mixture was heated
  5. temperatureunder reflux overnight
  6. customcollecting water in a Dean-Stark trap
  7. temperatureThe reaction mixture was cooled to 0°
  8. additiondiluted with ether
  9. filtrationThe resulting precipitate was collected by filtration
  10. customgiving 0.89 g
  11. customof 5-[N-(n-butyl)-2-oxo-3-pyrrolin-4-yl]amino-1-(pent-3-ynyl)-4-cyanopyrazole, which was used without further purification

Sources & evidence

ORD record
ord-11d27fd6d568406a971081c8fe747ce5
Source dataset
uspto-grants-1987_11
Patent number
US04705793

Reaction notes

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