Dimethyl 2,2-dimethyl-3-oxobutanedioate → HCID 178500123, compound

HRID 1529167Notes

Reaction equation

HRID 1529167 reaction equation
[CH3:1][C:2]([CH3:13])([C:7](=O)[C:8](OC)=[O:9])[C:3]([O:5][CH3:6])=[O:4].[CH:14]1([CH2:19][N:20]2[C:24]3=[N:25][CH:26]=[C:27]([F:29])[CH:28]=[C:23]3[C:22]([C:30](=[NH:33])[NH:31][NH2:32])=[N:21]2)[CH2:18][CH2:17][CH2:16][CH2:15]1>C(O)C>[CH:14]1([CH2:19][N:20]2[C:24]3=[N:25][CH:26]=[C:27]([F:29])[CH:28]=[C:23]3[C:22]([C:30]3[N:31]=[N:32][C:7]([C:2]([CH3:13])([CH3:1])[C:3]([O:5][CH3:6])=[O:4])=[C:8]([OH:9])[N:33]=3)=[N:21]2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 85519062Dimethyl 2,2-dimethyl-3-oxobutanedioateHCID 178512733HCID 178512733, compound

Product 1

HCID 178500123HCID 178500123, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

841 mg (4.473 mmol) of dimethyl 2,2-dimethyl-3-oxobutanedioate were initially charged in 20 ml of ethanol, and the mixture was heated to reflux. Subsequently, 1.070 g (2.982 mmol) of 1-(cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboximidohydrazide suspended in 26 ml of ethanol were added, and the mixture was boiled under reflux overnight. After cooling, the mixture was concentrated, taken up in acetonitrile and filtered. The filtrate was purified by preparative HPLC (mobile phase: acetonitrile/water, gradient 30:70→100:0). This gave 396 mg of the target compound (32% of theory).

Workup

  1. temperaturethe mixture was heated to reflux
  2. additionwere added
  3. temperatureunder reflux overnight
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated
  6. filtrationfiltered
  7. customThe filtrate was purified by preparative HPLC (mobile phase: acetonitrile/water, gradient 30:70→100:0)

Sources & evidence

ORD record
ord-9f5a1b8dc0f041e28dc2889b0ef01389
Source dataset
uspto-grants-2015_07
Patent number
US09090610B2

Reaction notes

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