Dicyclohexylcarbodiimide → 4-[[bis(1H-imidazol-2-ylmethyl)amino]methyl]-N-[4-[(dipropylamino)methyl]phenyl]naphthalene-1-carboxamide

HRID 348630Notes

Reaction equation

HRID 348630 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:25]([OH:27])=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.[CH2:53]([N:56]([CH2:60][C:61]1[CH:66]=[CH:65][C:64]([NH2:67])=[CH:63][CH:62]=1)[CH2:57][CH2:58][CH3:59])[CH2:54][CH3:55]>CN(C=O)C>[CH2:53]([N:56]([CH2:60][C:61]1[CH:66]=[CH:65][C:64]([NH:67][C:25]([C:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]([CH2:14][N:7]([CH2:6][C:2]3[NH:3][CH:4]=[CH:5][N:1]=3)[CH2:8][C:9]3[NH:13][CH:12]=[CH:11][N:10]=3)=[CH:16][CH:17]=2)=[O:27])=[CH:63][CH:62]=1)[CH2:57][CH2:58][CH3:59])[CH2:54][CH3:55]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 167770114-Dipropylaminomethyl-anilineHCID 210844614-{[bis(1H-imidazol-2-ylmethyl)amino]methyl}naphthalene-1-carboxylic Acid

Product 1

HCID 497715644-[[bis(1H-imidazol-2-ylmethyl)amino]methyl]-N-[4-[(dipropylamino)methyl]phenyl]naphthalene-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (130 mg) obtained in Example 36-4 was dissolved in DMF (3.0 ml) and then added with DCC (60.0 mg) and HOBt (40.0 mg), followed by stirring at room temperature for 2 hours. The compound (50.0 mg) obtained in Example 19-2 was added to the solution at room temperature, and the whole was stirred overnight. After completion of the reaction, insoluble matter was removed from the solution through a G4 glass filter and the solvent was distilled off. The residue was dissolved in chloroform and then washed with 1 mol/l hydrochloric acid. The organic layer was added with hydrochloric acid to separate the solution into layers. Then, the aqueous layer was added with a sodium hydroxide aqueous solution to adjust it to pH 12. The aqueous layer was subjected to extraction with chloroform, and the organic layer was dried with anhydrous sodium sulfate. Then, 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 (17.4 mg) of the subject compound as a white foamed compound.

Workup

  1. stirringthe whole was stirred overnight
  2. customAfter completion of the reaction, insoluble matter
  3. customwas removed from the solution through a G4 glass
  4. filtrationfilter
  5. distillationthe solvent was distilled off
  6. dissolutionThe residue was dissolved in chloroform
  7. washwashed with 1 mol/l hydrochloric acid
  8. additionThe organic layer was added with hydrochloric acid
  9. customto separate the solution into layers
  10. additionThen, the aqueous layer was added with a sodium hydroxide aqueous solution
  11. extractionThe aqueous layer was subjected to extraction with chloroform
  12. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  13. distillationThen, the solvent was distilled off
  14. additionSubsequently, the residue was treated with hydrochloric acid
  15. custompurified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-f9d604910fd34ee1bd350c8af0117f53
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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