Potassium Carbonate → HCID 45376866, compound

HRID 1184531Notes

Reaction equation

HRID 1184531 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[OH:10][C:11]1[CH:12]=[C:13](/[CH:19]=[CH:20]/[C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=2)=[O:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:10][C:11]1[CH:12]=[C:13](/[CH:19]=[CH:20]/[C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:3][C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)[CH:25]=2)=[O:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 67337921HCID 67337921, compound

Product 1

HCID 45376866HCID 45376866, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

3-Chloromethyl-pyridine hydrochloride (0.59 g 3.6 mmol) was added to a mixture of (E)-3-(3-hydroxy-4-methoxy-phenyl)-N-(3-hydroxy-phenyl)-acrylamide (0.39 g, 1.2 mmol) and potassium carbonate (0.83 g, 6.0 mmol) in dry DMF (5 mL) at RT. After stirring at 40° C. for 5 hrs, the resulting mixture was poured into ice, and the resulting precipitate was filtered, washed with water and dried. The resulting raw material was taken up, without further purification, with a 3N methanolic solution of hydrochloric acid (5 mL-15 mmols) and stirred at RT for 2.5 hrs, concentrated under reduced pressure, taken up with solvent an re-evaporated (3 times with MeOH and once with acetone) to give a residue that, after neutralization, was purified by silica gel column chromatography (eluant DCM/MeOH 98/2) to obtain 50 mg of the title (E)-3-(3-hydroxy-4-methoxy-phenyl)-N-[3-(pyridin-3-ylmethoxy)-phenyl]-acrylamide.

Workup

  1. additionthe resulting mixture was poured into ice
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customThe resulting raw material was taken up, without further purification, with a 3N methanolic solution of hydrochloric acid (5 mL-15 mmols)
  6. stirringstirred at RT for 2.5 hrs
  7. concentrationconcentrated under reduced pressure
  8. customan re-evaporated (3 times with MeOH
  9. customonce with acetone) to give a residue that, after neutralization
  10. customwas purified by silica gel column chromatography (eluant DCM/MeOH 98/2)

Sources & evidence

ORD record
ord-0cb118d53057426ca6400f807fcfb289
Source dataset
uspto-grants-2014_03
Patent number
US08669261B2

Reaction notes

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