Dicyclohexylcarbodiimide → 4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(3-dipropylaminopropyl)-benzamide

HRID 348604Notes

Reaction equation

HRID 348604 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[CH2:49]([N:52]([CH2:57][CH2:58][CH3:59])[CH2:53][CH2:54][CH2:55][NH2:56])[CH2:50][CH3:51]>CN(C=O)C>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:56][CH2:55][CH2:54][CH2:53][N:52]([CH2:57][CH2:58][CH3:59])[CH2:49][CH2:50][CH3:51])=[O:21])=[CH:22][CH:23]=1)[CH2:8][C:9]1[NH:13][CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 239005n,n-Dipropylpropane-1,3-diamineHCID 669419114-[N,N-bis-(imidazol-2-ylmethyl)aminomethyl]-benzoic Acid

Product 1

HCID 103438074-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(3-dipropylaminopropyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (190 mg) obtained in Example 2-2 was dissolved in DMF (3.0 ml) and added with DCC (189 mg), HOBt (124 mg), and the compound (96.9 mg) obtained in Example 22-3, followed by stirring overnight at room temperature. After completion of the reaction, the solvent was distilled off and the residue was then dissolved in chloroform, followed by separating the solution into layers by the addition of 1 mol/l hydrochloric acid. The aqueous layer was made basic with a 1 mol/l sodium hydroxide aqueous solution. Then, the solution was subjected to extraction with chloroform. The extract was washed with saturated saline solution and the organic layer was then dried with anhydrous sodium sulfate. The solvent was distilled off. Subsequently, the residue was treated with hydrochloric acid and then purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (84.8 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was then dissolved in chloroform
  4. customby separating the solution into layers
  5. additionby the addition of 1 mol/l hydrochloric acid
  6. extractionThen, the solution was subjected to extraction with chloroform
  7. washThe extract was washed with saturated saline solution
  8. dry with materialthe organic layer was then dried with anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. additionSubsequently, the residue was treated with hydrochloric acid
  11. custompurified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-a504a55952ac48419e885f08320a12fe
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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