Ethyl oxoacetate → HCID 178516809, compound

HRID 2278839Notes

Reaction equation

HRID 2278839 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14](=[NH:17])[NH:15][NH2:16])=[N:6]1.[O:22]=[CH:23][C:24](OCC)=O>C(O)C>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:15]=[N:16][CH:24]=[C:23]([OH:22])[N:17]=2)=[N:6]1

Participants

4

Reactant 2

HCID 70211Ethyl oxoacetateHCID 178512735HCID 178512735, compound

Product 1

HCID 178516809HCID 178516809, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

22.000 g (purity 68%, approx. 52.621 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidohydrazide in 220 ml of ethanol were initially introduced, admixed dropwise with 18.265 (89.455 mmol) of ethyl oxoacetate (50% strength solution in toluene) and heated under reflux overnight. The resulting suspension was concentrated on a rotary evaporator and stirred with diethyl ether. The solid was filtered off with suction and dried under high vacuum. Further purification was effected by chromatography on silica gel (mobile phase: dichloromethane/methanol, gradient 30:1→10:1). This gave 12.07 g of the target compound (purity 69%; 49% of theory).

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. concentrationThe resulting suspension was concentrated on a rotary evaporator
  4. filtrationThe solid was filtered off with suction
  5. customdried under high vacuum
  6. customFurther purification

Sources & evidence

ORD record
ord-93cae992da9c4f6d86d22c2472e18e3f
Source dataset
uspto-grants-2015_09
Patent number
US09133191B2

Reaction notes

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