Piperazine → HCID 178450871, compound

HRID 1463228Notes

Reaction equation

HRID 1463228 reaction equation
F[C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:5]2=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C1(C)C=CC=CC=1>[N:18]1([C:2]2[N:7]=[C:6]3[NH:8][N:9]=[C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:5]3=[CH:4][CH:3]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 178450870HCID 178450870, compound

Product 1

HCID 178450871HCID 178450871, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

t-Butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (3.00 g, 0.0126 mole) was dissolved in 100 mL of toluene containing 10.85 g of piperazine (0.126 mole) and refluxed overnight. The resultant precipitate was filtered off and distributed between an aqueous NaHCO3 solution and EtOAc and then the organic phase was dried and concentrated to give a product which was recrystallized from CH3CN to give 1.57 g, mp 190°-191° C. The toluene filtrate was washed with NaHCO3 solution and then concentrated and purified by flash chromatography (EtOAc:MeOH:Et3N/16:2:2) to give an additional 1.38 g of product (total yield 77%).

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe resultant precipitate was filtered off
  3. customthe organic phase was dried
  4. concentrationconcentrated
  5. customto give a product which
  6. customwas recrystallized from CH3CN
  7. customto give 1.57 g, mp 190°-191° C
  8. washThe toluene filtrate was washed with NaHCO3 solution
  9. concentrationconcentrated
  10. custompurified by flash chromatography (EtOAc:MeOH:Et3N/16:2:2)

Sources & evidence

ORD record
ord-c48339593c8d4211938b4992c055f936
Source dataset
uspto-grants-1994_04
Patent number
US05300498

Reaction notes

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