Hydrochloric Acid → HCID 53413168, compound

HRID 1753066Notes

Reaction equation

HRID 1753066 reaction equation
C(O[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([F:13])[C:11]=1[NH2:12])C.Cl>CCO>[F:13][C:10]1[C:11]2[NH:12][CH:4]=[CH:5][C:6]=2[CH:7]=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123348954HCID 123348954, compound

Product 1

HCID 53413168HCID 53413168, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(2-ethoxy-vinyl)-5-fluoro-pyridin-4-ylamine (Preparation 63, 3.6 g, 19.2 mmol) and concentrated HCl (10 mL) in EtOH (44 mL) was heated to reflux for 4 hours before cooling and concentrating in vacuo. The residue was basified with saturated aqueous NaHCO3 solution, extracted in DCM, the organic layer collected, dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 20-100% EtOAc in hexane to afford the title compound (1.7 g)

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. temperaturebefore cooling
  4. concentrationconcentrating in vacuo
  5. extractionextracted in DCM
  6. customthe organic layer collected
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified
  10. washeluting with 20-100% EtOAc in hexane

Sources & evidence

ORD record
ord-996d3db6451549c5aafd800d14c8c6ae
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

Loading…