2,5-Hexanedione → 3-(2,5-Dimethyl-1H-pyrrol-1-yl)-N-methoxy-N-methyl-1H-pyrazole-5-carboxamide

HRID 407783Notes

Reaction equation

HRID 407783 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([N:9]([O:11][CH3:12])[CH3:10])=[O:8])[NH:4][N:3]=1.[CH3:13][C:14](=O)[CH2:15][CH2:16][C:17](=O)[CH3:18]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:18][C:17]1[N:1]([C:2]2[CH:6]=[C:5]([C:7]([N:9]([O:11][CH3:12])[CH3:10])=[O:8])[NH:4][N:3]=2)[C:14]([CH3:13])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 80352,5-HexanedioneHCID 645248193-amino-N-methoxy-N-methyl-1H-pyrazole-5-carboxamide

Product 1

HCID 866840463-(2,5-Dimethyl-1H-pyrrol-1-yl)-N-methoxy-N-methyl-1H-pyrazole-5-carboxamideYield 65%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A 250-mL round-bottomed flask equipped with a magnetic stirrer and a Dean-Stark trap was charged with 150b (11.0 g, 1.0 eq., 64.7 mmol), hexane-2,5-dione (11.1 g, 1.5 eq., 97.2 mmol), p-toluenesulfonic acid monohydrate (558 mg, 0.05 eq., 3.24 mmol), and toluene (100 mL). The reaction mixture was refluxed overnight. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with 1:2 petroleum ether/ethyl acetate to afford 150c (10.4 g, 65%) as a white solid. MS-ESI: [M+H]+ 249.0

Workup

  1. customA 250-mL round-bottomed flask equipped with a magnetic stirrer
  2. temperatureThe reaction mixture was refluxed overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica-gel column chromatography
  5. washeluting with 1:2 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-2bb56152d365494b9e5f13ba5a04eab6
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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