Dimethyl 2,2-dimethyl-3-oxobutanedioate → HCID 178500124, compound

HRID 570522Notes

Reaction equation

HRID 570522 reaction equation
[CH3:1][C:2]([CH3:13])([C:7](=O)[C:8](OC)=[O:9])[C:3]([O:5][CH3:6])=[O:4].[F:14][C:15]1[CH:33]=[CH:32][CH:31]=[CH:30][C:16]=1[CH2:17][N:18]1[C:22]2[CH2:23][CH2:24][CH2:25][C:21]=2[C:20]([C:26](=[NH:29])[NH:27][NH2:28])=[N:19]1>C(O)C>[F:14][C:15]1[CH:33]=[CH:32][CH:31]=[CH:30][C:16]=1[CH2:17][N:18]1[C:22]2[CH2:23][CH2:24][CH2:25][C:21]=2[C:20]([C:26]2[N:27]=[N:28][C:7]([C:2]([CH3:13])([CH3:1])[C:3]([O:5][CH3:6])=[O:4])=[C:8]([OH:9])[N:29]=2)=[N:19]1

Participants

4

Reactant 2

HCID 85519062Dimethyl 2,2-dimethyl-3-oxobutanedioateHCID 178512734HCID 178512734, compound

Product 1

HCID 178500124HCID 178500124, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

218 mg (1.13 mmol) of dimethyl 2,2-dimethyl-3-oxobutanedioate were initially charged in 5 ml of ethanol and heated to reflux. Subsequently, 205 mg (0.75 mmol) of 1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboximidohydrazide suspended in 5 ml of ethanol were added and the mixture was boiled under reflux overnight. After cooling, the mixture was filtered, the filtercake was washed with a little ethanol and the filtrate was concentrated. The residue was purified by means of preparative HPLC (eluent: acetonitrile/water, gradient 20:80→100:0). 48 mg of the target compound were obtained (purity 54%; 8% of theory).

Workup

  1. temperatureheated to reflux
  2. additionwere added
  3. temperatureunder reflux overnight
  4. temperatureAfter cooling
  5. filtrationthe mixture was filtered
  6. washthe filtercake was washed with a little ethanol
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by means of preparative HPLC (eluent: acetonitrile/water, gradient 20:80→100:0)

Sources & evidence

ORD record
ord-09880d91a89c4072bd0e517a4373b864
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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