HCID 67327548, compound → HCID 86673398, compound

HRID 1023366Notes

Reaction equation

HRID 1023366 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9]/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([CH2:18]Cl)=[C:14]([CH3:20])[CH:13]=2)=[CH:4][CH:3]=1.[OH:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][C:29]2[C:34]([CH3:35])=[CH:33][C:32](/[CH:36]=[CH:37]/[C:38]([N:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)=[O:39])=[CH:31][C:30]=2[CH3:46])=[N:26][CH:27]=1>CN(C=O)C>[OH:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][C:29]2[C:34]([CH3:35])=[CH:33][C:32](/[CH:36]=[CH:37]/[C:38]([N:40]3[CH2:45][CH2:44][N:43]([CH2:18][C:15]4[CH:16]=[CH:17][C:12](/[CH:11]=[CH:10]/[CH2:9][O:8][C:5]5[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=5)=[CH:13][C:14]=4[CH3:20])[CH2:42][CH2:41]3)=[O:39])=[CH:31][C:30]=2[CH3:46])=[N:26][CH:27]=1

Participants

4

Reactant 2

HCID 67327548HCID 67327548, compoundHCID 67355599HCID 67355599, compound

Product 1

HCID 86673398HCID 86673398, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (E)-3-[4-(chloromethyl)-3-methylphenyl]prop-2-en-1-yl 4-methylphenyl ether (0.180 g) and (E)-3-{4-[(5-hydroxypyridin-2-yl)oxy]-3,5-dimethylphenyl}-1-(piperazin-1-yl)prop-2-en-1-one (0.222 g) in DMF (2 mL) was added KHCO3 (0.063 g) at room temperature under an Ar atmosphere. The mixture was heated at 100° C. for 3 hours, and then cooled to room temperature, and evaporated under reduced pressure. To the residue was added saturated aqueous NaHCO3, and the mixture was extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous Na2SO4. The residue was purified by silica gel column chromatography (AcOEt) to afford (2E)-3-{4-[(5-hydroxypyridin-2-yl)oxy]-3,5-dimethylphenyl}-1-(4-{2-methyl-4-[(1E)-3-(4-methylphenoxy)prop-1-en-1-yl]benzyl}piperazin-1-yl)prop-2-en-1-one (0.286 g) as a colorless powder.

Workup

  1. temperaturecooled to room temperature
  2. customevaporated under reduced pressure
  3. additionTo the residue was added saturated aqueous NaHCO3
  4. extractionthe mixture was extracted with AcOEt
  5. washThe organic layer was washed with saturated aqueous NaCl
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe residue was purified by silica gel column chromatography (AcOEt)

Sources & evidence

ORD record
ord-56fa750301f44cb6b86fe7dfe5217790
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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