Trifluoroacetic acid → HCID 178446248, compound

HRID 384069Notes

Reaction equation

HRID 384069 reaction equation
[CH3:1][C:2]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:27]=[C:28]([C:29]([F:32])([F:31])[F:30])[C:21]=23)[CH:15]=1)([CH2:12][CH3:13])[CH2:3][NH:4]C(=O)OC(C)(C)C.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]3[NH:26][N:27]=[C:28]([C:29]([F:31])([F:32])[F:30])[C:21]=23)[CH:15]=1)([CH2:12][CH3:13])[CH2:3][NH2:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57969739HCID 57969739, compound

Product 1

HCID 178446248HCID 178446248, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-butyl 2-methyl-2-(3-(3-(trifluoromethyl)-1-trityl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)butylcarbamate (148 mg, 0.2142 mmol) was dissolved in dry DCM (2 mL) and cooled in an ice-bath. triethylsilane (99.63 mg, 136.9 μL, 0.8568 mmol) was added followed slowly dropwise by TFA (2 mL,). The resulting mixture was stirred at 0° C. for ˜1 hour 50 minutes. The reaction mixture was concentrated under reduced pressure to give a light brown solid/gum. This material was partitioned with ether and brine. The ether layer was washed with 1M HCl (2×10 mL) and the combined aqueous layer was basified with saturated NaHCO3 and extracted with EtOAc (3×10 mL). The combined EtOAc was dried over Na2SO4, filtered and concentrated under reduced pressure to give a colourless gum (56.5 mg). This material was purified by column chromatography (4.5% MeOH/0.5% NH4OH in DCM, ˜75 mL silica, loaded in DCM) to give a white powder (15 mg, 20% Yield).

Workup

  1. temperaturecooled in an ice-bath
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give a light brown solid/gum
  4. customThis material was partitioned with ether and brine
  5. washThe ether layer was washed with 1M HCl (2×10 mL)
  6. extractionextracted with EtOAc (3×10 mL)
  7. dry with materialThe combined EtOAc was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76d360991b8d4550b4f43b9c808a2989
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

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