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

HRID 348637Notes

Reaction equation

HRID 348637 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][N:8]([CH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=1)[CH2:9][C:10]1[N:11]([CH3:15])[CH:12]=[CH:13][N:14]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[CH2:51]([N:54]([CH2:60][CH2:61][CH3:62])[CH2:55][CH2:56][CH2:57][CH2:58][NH2:59])[CH2:52][CH3:53]>CN(C=O)C>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][N:8]([CH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:59][CH2:58][CH2:57][CH2:56][CH2:55][N:54]([CH2:60][CH2:61][CH3:62])[CH2:51][CH2:52][CH3:53])=[O:23])=[CH:19][CH:18]=1)[CH2:9][C:10]1[N:11]([CH3:15])[CH:12]=[CH:13][N:14]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7138396N,N-dipropylbutane-1,4-diamineHCID 669418054-{[bis(1-methyl-1H-imidazol-2-ylmethyl)amino]methyl}-benzoic Acid

Product 1

HCID 588019114-{[bis(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminobutyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

The compound (75.0 mg) obtained in Example 40-1 was dissolved in DMF (2.0 ml) and then added with DCC (46.0 mg) and HOBt (36.0 mg), followed by stirring for 6 hours. A solution of the compound (76.0 mg) obtained in Example 1-2 in DMF was added to the reaction system and then the whole was stirred for 15 hours. After completion of the reaction, DMF was distilled off and the residue was then dissolved in chloroform, followed by extraction with 1 mol/l hydrochloric acid. The aqueous layer was added with a 1 mol/l sodium hydroxide aqueous solution and then extracted with chloroform. The extract was dried with anhydrous magnesium sulfate and the solvent was then distilled off, followed by treating with hydrochloric acid. Subsequently, the treated product was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (23.9 mg) of the subject compound as a white solid.

Workup

  1. stirringthe whole was stirred for 15 hours
  2. distillationwas distilled off
  3. dissolutionthe residue was then dissolved in chloroform
  4. extractionfollowed by extraction with 1 mol/l hydrochloric acid
  5. additionThe aqueous layer was added with a 1 mol/l sodium hydroxide aqueous solution
  6. extractionextracted with chloroform
  7. dry with materialThe extract was dried with anhydrous magnesium sulfate
  8. distillationthe solvent was then distilled off
  9. additionby treating with hydrochloric acid
  10. customSubsequently, the treated product was purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-03d953a9c8a84e2aa261bd318474ed65
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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