1-Hydroxybenzotriazole → 4-[[bis(1H-imidazol-2-ylmethyl)amino]methyl]-N-[3-[(dipropylamino)methyl]phenyl]benzamide

HRID 348622Notes

Reaction equation

HRID 348622 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].[NH:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH2:21][N:22]([CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1)[CH2:23][C:24]1[NH:25][CH:26]=[CH:27][N:28]=1.C1C=CC2N(O)N=NC=2C=1.N=C=N>CN(C=O)C>[NH:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH2:21][N:22]([CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[C:9]([CH2:8][N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])[CH:10]=2)=[O:35])=[CH:32][CH:31]=1)[CH2:23][C:24]1[NH:28][CH:27]=[CH:26][N:25]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 230793273-DipropylaminomethylanilineHCID 669419114-[N,N-bis-(imidazol-2-ylmethyl)aminomethyl]-benzoic Acid

Product 1

HCID 104136194-[[bis(1H-imidazol-2-ylmethyl)amino]methyl]-N-[3-[(dipropylamino)methyl]phenyl]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (51.6 mg) obtained in Example 33-2, the compound (117 mg) obtained in Example 2-2, and HOBt (50.0 mg) were dissolved in anhydrous DMF (2.5 ml). Then, the solution was added with PS-carbodiimide (manufactured by Argonaut Technologies, Inc.) (373.1 mg), followed by stirring at room temperature for 17 hours. After completion of the reaction, the mixture was filtrated and the solvent was then distilled off. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution and saturated saline solution. The residue was dried with anhydrous magnesium sulfate and the solvent was distilled off, followed by treatment with hydrochloric acid. The residue was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (18.5 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtrated
  3. distillationthe solvent was then distilled off
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with a 1 mol/l sodium hydroxide aqueous solution and saturated saline solution
  6. dry with materialThe residue was dried with anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-879097c131f848a995cf614a125f2125
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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