Dicyclohexylcarbodiimide → 4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethylphenyl)-N-methylbenzamide

HRID 348666Notes

Reaction equation

HRID 348666 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](O)=[O:20])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH2:49]([N:52]([CH2:56][C:57]1[CH:62]=[CH:61][C:60]([NH:63][CH3:64])=[CH:59][CH:58]=1)[CH2:53][CH2:54][CH3:55])[CH2:50][CH3:51]>CN(C=O)C>[NH:10]1[CH:11]=[CH:12][N:13]=[C:9]1[CH2:8][N:7]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([N:63]([C:60]2[CH:61]=[CH:62][C:57]([CH2:56][N:52]([CH2:49][CH2:50][CH3:51])[CH2:53][CH2:54][CH3:55])=[CH:58][CH:59]=2)[CH3:64])=[O:20])=[CH:22][CH:23]=1)[CH2:6][C:2]1[NH:3][CH:4]=[CH:5][N:1]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 23079200N-(4-dipropylaminomethylphenyl)-methylamineHCID 669419114-[N,N-bis-(imidazol-2-ylmethyl)aminomethyl]-benzoic Acid

Product 1

HCID 104364834-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethylphenyl)-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The compound (278 mg) obtained in Example 2-2, HOBt (95.9 mg), and DCC (147 mg) were dissolved in anhydrous DMF (11.0 ml), followed by stirring at room temperature for 19 hours. Then, the solution was added with a solution (1.2 ml) of the compound (128 mg) obtained in Example 68-1 in DMF and stirred at room temperature for 20 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and added with 1 mol/l hydrochloric acid to separate the solution into layers. The aqueous layer was added with a 1 mol/l sodium hydroxide aqueous solution to adjust the solution to pH 11. The aqueous layer was extracted with chloroform and the organic layer was then dried with anhydrous magnesium sulfate. After having been treated with hydrochloric acid, the product was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (10.2 mg) of the subject compound as a white solid.

Workup

  1. stirringstirred at room temperature for 20 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. additionadded with 1 mol/l hydrochloric acid
  6. customto separate the solution into layers
  7. additionThe aqueous layer was added with a 1 mol/l sodium hydroxide aqueous solution
  8. extractionThe aqueous layer was extracted with chloroform
  9. dry with materialthe organic layer was then dried with anhydrous magnesium sulfate
  10. additionAfter having been treated with hydrochloric acid
  11. customthe product was purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-b4c8350561ed4b9d822255fcbd4923d0
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

Loading…