Trifluoroacetic acid → HCID 22063683, compound

HRID 1828436Notes

Reaction equation

HRID 1828436 reaction equation
[Br:1][C:2]1[C:6]([CH2:7][CH3:8])=[CH:5][S:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH:17]C(=O)OC(C)(C)C)[CH:12]=1.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[C:6]([CH2:7][CH3:8])=[CH:5][S:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22063791HCID 22063791, compound

Product 1

HCID 22063683HCID 22063683, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl N-{4-[2-(3-bromo-4-ethyl-2-thienyl)ethyl]-2-pyridyl}carbamate (1.34 g, 4.04 mmol) dissolved in dichloromethane (40 ml) was added with trifluoroacetic acid (40 ml) at 0° C. and stirred at 0° C. for 3 hours. The reaction solution was concentrated under reduced pressure, neutralized with saturated sodium hydrogencarbonate and extracted with chloroform, and then the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:ethyl acetate=3:1→1:1→ethyl acetate only) to obtain 524 mg (56%) of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. extractionextracted with chloroform
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform

Sources & evidence

ORD record
ord-5f285d971f19481a8a14d3cee934a833
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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