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

HRID 348600Notes

Reaction equation

HRID 348600 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)[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:15][C:12]2[CH:13]=[CH:14][C:9]([CH2:8][N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])=[CH:10][CH:11]=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 167770114-Dipropylaminomethyl-anilineHCID 669419114-[N,N-bis-(imidazol-2-ylmethyl)aminomethyl]-benzoic Acid

Product 1

HCID 99834204-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethylphenyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (57.2 mg) obtained in Example 19-2, the compound (106 mg) obtained in Example 2-2, and HOBt (162 mg) were dissolved in anhydrous DMF (2.5 ml) and then added with PS-carbodiimide (manufactured by Argonaut Technologies, Inc.) (419 mg), followed by stirring at room temperature for 12 hours. After completion of the reaction, the solution was filtrated and the solvent was then distilled off. The residue was dissolved in chloroform and then washed with 1 mol/l sodium hydroxide and saturated saline solution, followed by drying with anhydrous magnesium sulfate. The solvent was distilled off and the residue was then treated with hydrochloric acid. Subsequently, the residue was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (18.3 mg) of the subject compound as a yellow solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe solution was filtrated
  3. distillationthe solvent was then distilled off
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with 1 mol/l sodium hydroxide and saturated saline solution
  6. dry with materialby drying with anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. additionthe residue was then treated with hydrochloric acid
  9. customSubsequently, the residue was purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-312296f3d98d4aa385316e73e1efc403
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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