3-Phenylprop-2-En-1-Ol → [(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid cinnamyl ester

HRID 2080860Notes

Reaction equation

HRID 2080860 reaction equation
Cl.[CH2:2]([N:5]([CH2:37][CH2:38][CH3:39])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:33][C:34]([OH:36])=[O:35])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]([CH2:27][C:28]2[NH:29][CH:30]=[CH:31][N:32]=2)[CH2:20][C:21]2[N:22]([CH3:26])[CH:23]=[CH:24][N:25]=2)=[CH:14][CH:13]=1)[CH2:3][CH3:4].[CH2:40](O)[CH:41]=[CH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C>[CH2:40]([O:35][C:34](=[O:36])[CH2:33][N:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:2][CH2:3][CH3:4])[CH2:37][CH2:38][CH3:39])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]([CH2:27][C:28]2[NH:29][CH:30]=[CH:31][N:32]=2)[CH2:20][C:21]2[N:22]([CH3:26])[CH:23]=[CH:24][N:25]=2)=[CH:14][CH:13]=1)[CH:41]=[CH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 3083-Phenylprop-2-En-1-OlHCID 313Hydrochloric AcidHCID 11540944[(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid

Product 1

HCID 67103573[(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid cinnamyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The hydrochloride (203 mg) of the compound obtained in Example 65-1 was dissolved in DMF (3.0 ml) and added with cinnamyl alcohol (73.9 μl) and the whole was refluxed overnight under heating. After completion of the reaction, the solvent was distilled off. The resultant was dissolved in chloroform and added with a saturated aqueous sodium hydrogen carbonate solution and the whole was stirred for a while. The solution was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (19.1 mg) of the subject compound as a brownish-red solid.

Workup

  1. temperaturethe whole was refluxed overnight
  2. temperatureunder heating
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off
  5. dissolutionThe resultant was dissolved in chloroform
  6. additionadded with a saturated aqueous sodium hydrogen carbonate solution
  7. extractionThe solution was subjected to extraction with chloroform
  8. washwashed with a saturated saline solution
  9. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  10. distillationThe solvent was distilled off
  11. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  12. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-bd3c4d726a444673b43fbf70946171eb
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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