Dicyclohexylcarbodiimide → 4-(4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzoyl)-(2-dipropylaminoethyl)-piperazine

HRID 348682Notes

Reaction equation

HRID 348682 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.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[CH2:49]([N:52]([CH2:61][CH2:62][CH3:63])[CH2:53][CH2:54][N:55]1[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]1)[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:23]=[CH:22][C:18]([C:19]([N:58]2[CH2:59][CH2:60][N:55]([CH2:54][CH2:53][N:52]([CH2:61][CH2:62][CH3:63])[CH2:49][CH2:50][CH3:51])[CH2:56][CH2:57]2)=[O:20])=[CH:17][CH:16]=1)[CH2:6][C:2]1[NH:1][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2736329N-(2-(Piperazin-1-yl)ethyl)-N-propylpropan-1-amineHCID 669419114-[N,N-bis-(imidazol-2-ylmethyl)aminomethyl]-benzoic Acid

Product 1

HCID 210844184-(4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-benzoyl)-(2-dipropylaminoethyl)-piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (103.8 mg) obtained in Example 2-2 was dissolved in DMF (3.1 ml) and then added with DCC (68.8 mg) and HOBt (45.0 mg), followed by stirring at room temperature for 10 days. The solution was added with 1-(2-dipropylaminoethyl)piperazine (71.1 mg) and further stirred at the same temperature for 4 days. The reaction solvent was distilled off and the residue was then added with 1 mol/l hydrochloric acid, followed by washing with chloroform. The aqueous layer was adjusted to pH 12 with a 1 mol/l sodium hydroxide aqueous solution and then subjected to separation/extraction with chloroform. The 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) and treated with hydrochloride acid, thereby obtaining hydrochloride (52.5 mg) of the subject compound as a white solid.

Workup

  1. stirringfurther stirred at the same temperature for 4 days
  2. distillationThe reaction solvent was distilled off
  3. additionthe residue was then added with 1 mol/l hydrochloric acid
  4. washby washing with chloroform
  5. extractionsubjected to separation/extraction with chloroform
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)
  9. additiontreated with hydrochloride acid

Sources & evidence

ORD record
ord-6d5a55da8ff642ef95f60709c7cf0619
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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