Trifluoroacetic acid → HCID 57969693, compound

HRID 1920877Notes

Reaction equation

HRID 1920877 reaction equation
[CH3:1][N:2]([CH3:42])[CH2:3][C:4]([CH3:41])([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[N:19](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:20]=[CH:21][C:14]=23)[CH:8]=1)[CH2:5][CH3:6].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:19]1[C:15]2=[N:16][CH:17]=[CH:18][C:13]([C:9]3[CH:8]=[C:7]([C:4]([CH3:41])([CH2:5][CH3:6])[CH2:3][N:2]([CH3:1])[CH3:42])[CH:12]=[CH:11][CH:10]=3)=[C:14]2[CH:21]=[N:20]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57969826HCID 57969826, compound

Product 1

HCID 57969693HCID 57969693, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N,2-trimethyl-2-(3-(1-trityl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)butan-1-amine (89.3 mg, 0.1621 mmol) was dissolved in dry DCM (2 mL) and cooled in an ice-bath. Triethylsilane (75.39 mg, 103.6 μL, 0.6484 mmol) was added followed by TFA (2 mL). The resultant mixture was stirred at 0° C. for 85 minutes and then concentrated under vacuo. The residue was partitioned between EtOAc and 1:1 c.HCl/water. The organic layer was extracted further with 1:1 c.HCl/water (3×20 mL) and the combined aqueous material was cooled in an ice-bath and carefully basified with 5M NaOH. The basic aqueous mixture was extracted with EtOAc (3×20 mL) and the combined organics were washed with brine (3×10 mL), dried over Na2SO4, filtered and concentrated under vacuo to give a yellow gum. This was purified by column chromatography (10% MeOH in DCM, ˜75 mL silica) to give a colourless gum which was triturated with pentane to give a white powder (12.3 mg, 24% Yield).

Workup

  1. temperaturecooled in an ice-bath
  2. concentrationconcentrated under vacuo
  3. customThe residue was partitioned between EtOAc and 1:1 c
  4. extractionThe organic layer was extracted further with 1:1 c
  5. temperatureHCl/water (3×20 mL) and the combined aqueous material was cooled in an ice-bath
  6. extractionThe basic aqueous mixture was extracted with EtOAc (3×20 mL)
  7. washthe combined organics were washed with brine (3×10 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuo
  11. customto give a yellow gum
  12. customThis was purified by column chromatography (10% MeOH in DCM, ˜75 mL silica)
  13. customto give a colourless gum which
  14. customwas triturated with pentane

Sources & evidence

ORD record
ord-bd277eb45f31403bba3297f60d21a5dc
Source dataset
uspto-grants-2012_05
Patent number
US08173635B2

Reaction notes

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