Hydrochloric Acid → 2-[(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-N,N-dimethyl-acetamide

HRID 2080870Notes

Reaction equation

HRID 2080870 reaction equation
Cl.[CH2:2]([N:5]([CH2:37][CH2:38][CH3:39])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:33]C(O)=O)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]([CH2:27][C:28]2[NH:29][CH:30]=[CH:31][N:32]=2)[CH2:20][C:21]2[N:22]([CH3:26])[CH:23]=[CH:24][N:25]=2)=[CH:14][CH:13]=1)[CH2:3][CH3:4].OCCN1C(=O)CCC1=O.[CH3:50][N:51]([CH:53]=[O:54])[CH3:52]>>[CH2:37]([N:5]([CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][N:19]([CH2:27][C:28]2[NH:29][CH:30]=[CH:31][N:32]=2)[CH2:20][C:21]2[N:22]([CH3:26])[CH:23]=[CH:24][N:25]=2)=[CH:16][CH:17]=1)[CH2:33][C:53]([N:51]([CH3:52])[CH3:50])=[O:54])[CH2:38][CH3:39]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 236334N-(2-Hydroxyethyl)succinimideHCID 11540944[(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid

Product 1

HCID 116639902-[(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-N,N-dimethyl-acetamide

Procedure

The hydrochloride (190 mg) of the compound obtained in Example 65-1 was dissolved in DMF (5.0 ml) and added with N-(2-hydroxyethyl)-succinimide (57.8 mg) and the whole was refluxed under heating for 4 hours. After completion of the reaction, the solvent was distilled off. The resultant was dissolved in chloroform and added with a saturated aqueous sodium hydrogen carbonate solution and the whole was stirred for a while. The solution was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining a hydrochloride (82.5 mg) of the subject compound as a pale-yellow solid.

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 4 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off
  5. dissolutionThe resultant was dissolved in chloroform
  6. additionadded with a saturated aqueous sodium hydrogen carbonate solution
  7. extractionThe solution was subjected to extraction with chloroform
  8. washwashed with a saturated saline solution
  9. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  10. distillationThe solvent was distilled off
  11. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  12. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-03d2d094ac364e78807a29a88405e857
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

Loading…