Trifluoroacetic acid → 2-chloro-1-(8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone

HRID 2383434Notes

Reaction equation

HRID 2383434 reaction equation
[Cl:1][CH:2]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:3]([N:5]1[CH2:14][C:13]2[CH:12]=[N:11][C:10]3[N:15](CC4C=CC(OC)=CC=4)[N:16]=[CH:17][C:9]=3[C:8]=2[CH2:7][CH2:6]1)=[O:4].FC(F)(F)C(O)=O.O1CCOCC1>C1(C)C=CC=CC=1>[Cl:1][CH:2]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:3]([N:5]1[CH2:14][C:13]2[CH:12]=[N:11][C:10]3[NH:15][N:16]=[CH:17][C:9]=3[C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 312751,4-DioxaneHCID 594904292-chloro-1-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone

Product 1

HCID 594906052-chloro-1-(8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanoneYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To 2-chloro-1-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone (0.60 g, 1.34 mmol) was added trifluoroacetic acid (2 mL). The reaction mixture was heated at 65° C. for 16 hours. On completion of the reaction, 1,4-dioxane (5 mL) and toluene (5 mL) were added and the solvent removed under reduced pressure to give the crude product. The crude product was then partitioned between dichloromethane (20 mL) and water (20 mL). The organic layer was separated, washed with brine (2×10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography (SiO2, gradient 60% EtOAc in hexane to 80% EtOAc in hexane) to give the pure desired product, 2-chloro-1-(8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-phenylethanone as a white foamy solid (0.360 g, 83%). LCMS [M+H]: 327.

Workup

  1. additionwere added
  2. customthe solvent removed under reduced pressure
  3. customto give the crude product
  4. customThe crude product was then partitioned between dichloromethane (20 mL) and water (20 mL)
  5. customThe organic layer was separated
  6. washwashed with brine (2×10 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by flash column chromatography (SiO2, gradient 60% EtOAc in hexane to 80% EtOAc in hexane)

Sources & evidence

ORD record
ord-963ff669173b4880bca19bc111489f7b
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

Loading…