Dimethyl 2,2-dimethyl-3-oxobutanedioate → HCID 178500127, compound

HRID 570530Notes

Reaction equation

HRID 570530 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:35]=[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[CH:35]=[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-oxobutanedioateHCID 178432595HCID 178432595, compound

Product 1

HCID 178500127HCID 178500127, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

615 mg (3.27 mmol) of dimethyl 2,2-dimethyl-3-oxobutanedioate were initially charged in 13 ml of ethanol and heated to reflux. Subsequently, 652 mg (2.18 mmol) of 1-(2-fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboximidohydrazide suspended in 13 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 30:70→100:0). 182 mg of the target compound were obtained (19% 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 30:70→100:0)

Sources & evidence

ORD record
ord-ebe7556610ab4032a8de71bef91e7ac9
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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