1-Hydroxybenzotriazole → 4-(4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzoyl)-piperazin-1-carboxylic acid t-butyl ester

HRID 348617Notes

Reaction equation

HRID 348617 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.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:46]([N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1)([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47]>CN(C=O)C>[C:49]([O:48][C:46]([N:53]1[CH2:54][CH2:55][N:56]([C:19](=[O:20])[C:18]2[CH:22]=[CH:23][C:15]([CH2:14][N:7]([CH2:6][C:2]3[NH:1][CH:5]=[CH:4][N:3]=3)[CH2:8][C:9]3[NH:10][CH:11]=[CH:12][N:13]=3)=[CH:16][CH:17]=2)[CH2:57][CH2:58]1)=[O:47])([CH3:52])([CH3:51])[CH3:50]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 669419114-[N,N-bis-(imidazol-2-ylmethyl)aminomethyl]-benzoic Acid

Product 1

HCID 669414774-(4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzoyl)-piperazin-1-carboxylic acid t-butyl esterYield 17.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (500 mg) obtained in Example 2-2 was dissolved in DMF (10 ml) and added with WSCI hydrochloride (257 mg), HOBt (181 mg), and 1-Boc piperazine (manufactured by Aldrich Corporation) (249 mg), followed by stirring at room temperature for 3 days. After completion of the reaction, the solvent was distilled off and the residue was then dissolved in chloroform for extraction, followed by washing with distilled water, a 1 mol/l sodium hydroxide aqueous solution, and saturated saline solution. The resulting organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining the subject compound (111 mg) as a yellow oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was then dissolved in chloroform for extraction
  4. washby washing with distilled water
  5. dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was then purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-ac1000f3fc9742b08be21a43badc6f29
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

Loading…