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

HRID 1173846Notes

Reaction equation

HRID 1173846 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]([OH:21])=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.[CH2:49]([N:52]([CH2:67][CH2:68][CH3:69])[C:53]1[CH:58]=[CH:57][C:56]([NH:59]C(OC(C)(C)C)=O)=[CH:55][CH:54]=1)[CH2:50][CH3:51]>CN(C=O)C>[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]([NH:59][C:56]2[CH:55]=[CH:54][C:53]([N:52]([CH2:67][CH2:68][CH3:69])[CH2:49][CH2:50][CH3:51])=[CH:58][CH:57]=2)=[O:21])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 23079266N,N-dipropyl-N'-Boc-1,4-phenylenediamineHCID 669419114-[N,N-bis-(imidazol-2-ylmethyl)aminomethyl]-benzoic Acid

Product 1

HCID 100510774-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminophenyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (300 mg) obtained in Example 2-2 was dissolved in DMF (10 ml) and added with DCC (298 mg), HOBt (195 mg), and the compound (185 mg) obtained in Example 15-1, followed by stirring overnight at room temperature. After completion of the reaction, the solvent was distilled off and the residue was then dissolved in chloroform, followed by separating the solution into layers by the addition of 1 mol/l hydrochloric acid. The aqueous layer was made basic by the addition of a 1 mol/l sodium hydroxide aqueous solution. Then, the solution was subjected to extraction with chloroform. The extract was washed with saturated saline solution and the organic layer was then dried with anhydrous sodium sulfate. 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 (96.4 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was then dissolved in chloroform
  4. customby separating the solution into layers
  5. additionby the addition of 1 mol/l hydrochloric acid
  6. additionThe aqueous layer was made basic by the addition of a 1 mol/l sodium hydroxide aqueous solution
  7. extractionThen, the solution was subjected to extraction with chloroform
  8. washThe extract was washed with saturated saline solution
  9. dry with materialthe organic layer was then dried with anhydrous sodium sulfate
  10. distillationThe solvent was distilled off
  11. additionSubsequently, the residue was treated with hydrochloric acid
  12. custompurified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-d1dd212aa27744748fd644bf5e7cf26d
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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