1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53361736, compound

HRID 1023367Notes

Reaction equation

HRID 1023367 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[C:21]([CH3:22])=[CH:20][C:19](/[CH:23]=[CH:24]/[C:25](O)=[O:26])=[CH:18][C:17]=3[CH3:28])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.Cl.Cl.[CH3:33][C:34]1[CH:56]=[CH:55][C:37]([O:38][CH2:39]/[CH:40]=[CH:41]/[C:42]2[CH:54]=[CH:53][C:45]([CH2:46][N:47]3[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]3)=[CH:44][CH:43]=2)=[CH:36][CH:35]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCN(CC)CC>[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[C:17]([CH3:28])=[CH:18][C:19](/[CH:23]=[CH:24]/[C:25]([N:50]4[CH2:49][CH2:48][N:47]([CH2:46][C:45]5[CH:53]=[CH:54][C:42](/[CH:41]=[CH:40]/[CH2:39][O:38][C:37]6[CH:36]=[CH:35][C:34]([CH3:33])=[CH:56][CH:55]=6)=[CH:43][CH:44]=5)[CH2:52][CH2:51]4)=[O:26])=[CH:20][C:21]=3[CH3:22])=[N:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 67326998HCID 67326998, compoundHCID 86673399HCID 86673399, compound

Product 1

HCID 53361736HCID 53361736, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of (E)-3-[4-({5-[(4-methoxybenzyl)oxy]pyridin-2-yl}oxy)-3,5-dimethylphenyl]prop-2-enoic acid (0.122 g) and 1-{4-[(E)-3-(4-methylphenoxy)prop-1-en-1-yl]benzyl}piperazine dihydrochloride (0.119 g) in DMF (2 mL) were added Et3N (0.08 mL), WSC (0.070 g), and HOBT (0.055 g) at room temperature under an Ar atmosphere. The mixture was stirred at room temperature for 14 hours, 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). The resulting powder was crystallized from EtOH (10 mL) to give (2E)-3-[4-({5-[(4-methoxybenzyl)oxy]pyridin-2-yl}oxy)-3,5-dimethylphenyl]-1-(4-{4-[(1E)-3-(4-methylphenoxy)prop-1-en-1-yl]benzyl}piperazin-1-yl)prop-2-en-1-one (0.195 g) as a colorless powder.

Workup

  1. customevaporated under reduced pressure
  2. additionTo the residue was added saturated aqueous NaHCO3
  3. extractionthe mixture was extracted with AcOEt
  4. washThe organic layer was washed with saturated aqueous NaCl
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (AcOEt)
  8. customThe resulting powder was crystallized from EtOH (10 mL)

Sources & evidence

ORD record
ord-42a0731c0de94ebf818b2d123a29f6f4
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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