Dimethyl 2,2-dimethyl-3-oxobutanedioate → HCID 178500130, compound

HRID 570536Notes

Reaction equation

HRID 570536 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[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:16]=1[CH2:17][N:18]1[C:22]2=[N:23][C:24]([CH3:27])=[N:25][CH:26]=[C:21]2[C:20]([C:28](=[NH:31])[NH:29][NH2:30])=[N:19]1>C(O)C>[F:14][C:15]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:16]=1[CH2:17][N:18]1[C:22]2=[N:23][C:24]([CH3:27])=[N:25][CH:26]=[C:21]2[C:20]([C:28]2[N:29]=[N:30][C:7]([C:2]([CH3:13])([CH3:1])[C:3]([O:5][CH3:6])=[O:4])=[C:8]([OH:9])[N:31]=2)=[N:19]1

Participants

4

Reactant 2

HCID 85519062Dimethyl 2,2-dimethyl-3-oxobutanedioate2×HCID 178432596HCID 178432596, compound

Product 1

HCID 178500130HCID 178500130, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

374 mg (1.985 mmol) of dimethyl 2,2-dimethyl-3-oxobutanedioate were initially charged in 8 ml of ethanol and heated to reflux. Subsequently, 420 mg (1.324 mmol) of 1-(2,3-difluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidohydrazide suspended in 8 ml of ethanol were added and the mixture was heated to reflux overnight. Another 299 mg (1.588 mmol) of dimethyl 2,2-dimethyl-3-oxobutanedioate dissolved in 3 ml of ethanol were added and the mixture was boiled under reflux overnight. After cooling, the mixture was filtered and purified directly by means of preparative HPLC (eluent: acetonitrile/water, gradient 30:70→100:0). 163 mg of the target compound were obtained (purity 89%; 24% of theory).

Workup

  1. temperatureheated to reflux
  2. additionwere added
  3. temperaturethe mixture was heated
  4. temperatureto reflux overnight
  5. additionwere added
  6. temperatureunder reflux overnight
  7. temperatureAfter cooling
  8. filtrationthe mixture was filtered
  9. custompurified directly by means of preparative HPLC (eluent: acetonitrile/water, gradient 30:70→100:0)

Sources & evidence

ORD record
ord-ab43d119f4bf46c0a3753bf19fdc624a
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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