Diisopropylethylamine → HCID 53361130, compound

HRID 1023375Notes

Reaction equation

HRID 1023375 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([O:14][C:15]3[C:20]([CH3:21])=[CH:19][C:18](/[CH:22]=[CH:23]/[C:24]([N:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)=[O:25])=[CH:17][C:16]=3[CH3:32])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH2:43]/[CH:44]=[CH:45]/[C:46]2[CH:51]=[CH:50][C:49]([CH2:52]Cl)=[CH:48][C:47]=2[CH3:54])=[CH:38][CH:37]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([O:14][C:15]3[C:20]([CH3:21])=[CH:19][C:18](/[CH:22]=[CH:23]/[C:24]([N:26]4[CH2:31][CH2:30][N:29]([CH2:52][C:49]5[CH:50]=[CH:51][C:46](/[CH:45]=[CH:44]/[CH2:43][O:42][C:39]6[CH:38]=[CH:37][C:36]([CH3:35])=[CH:41][CH:40]=6)=[C:47]([CH3:54])[CH:48]=5)[CH2:28][CH2:27]4)=[O:25])=[CH:17][C:16]=3[CH3:32])=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67327070HCID 67327070, compoundHCID 67328183HCID 67328183, compound

Product 1

HCID 53361130HCID 53361130, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-[4-({5-[(4-fluorobenzyl)oxy]pyridin-2-yl}oxy)-3,5-dimethylphenyl]-1-(piperazin-1-yl)prop-2-en-1-one (0.328 g) and (E)-3-[4-(chloromethyl)-2-methylphenyl]prop-2-en-1-yl 4-methylphenyl ether (0.204 g) in DMF (2 mL) was added DIPEA (0.13 mL) at room temperature under an Ar atmosphere. The mixture was stirred at room temperature for 20.5 hours, and then heated at 50° C. for 1 hour, 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, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt) to afford (2E)-3-[4-({5-[(4-fluorobenzyl)oxy]pyridin-2-yl}oxy)-3,5-dimethylphenyl]-1-(4-{3-methyl-4-[(1E)-3-(4-methylphenoxy)prop-1-en-1-yl]benzyl}piperazin-1-yl)prop-2-en-1-one (0.370 g) as a colorless oil.

Workup

  1. temperatureheated at 50° C. for 1 hour
  2. temperaturecooled to room temperature
  3. customevaporated under reduced pressure
  4. additionTo the residue was added saturated aqueous NaHCO3
  5. extractionthe mixture was extracted with AcOEt
  6. washThe organic layer was washed with saturated aqueous NaCl
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (AcOEt)

Sources & evidence

ORD record
ord-dbcf374599fd42c8b7a22d7cb1e98c7e
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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