2-Methoxyethanol → [(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid-2-methoxy-ethyl ester

HRID 2080859Notes

Reaction equation

HRID 2080859 reaction equation
[CH2:1]([N:4]([CH2:36][CH2:37][CH3:38])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:32][C:33]([OH:35])=[O:34])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]([CH2:26][C:27]2[NH:28][CH:29]=[CH:30][N:31]=2)[CH2:19][C:20]2[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=2)=[CH:13][CH:12]=1)[CH2:2][CH3:3].[CH3:39][O:40][CH2:41][CH2:42]O>>[CH3:39][O:40][CH2:41][CH2:42][O:34][C:33](=[O:35])[CH2:32][N:9]([CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:36][CH2:37][CH3:38])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]([CH2:26][C:27]2[NH:28][CH:29]=[CH:30][N:31]=2)[CH2:19][C:20]2[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=2)=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 80192-MethoxyethanolHCID 11540944[(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid

Product 1

HCID 11577844[(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid-2-methoxy-ethyl ester

Conditions

Temperature
80 °C

Procedure

The compound (190.7 mg) obtained in Example 65-1 was dissolved in 2-methoxyethanol (4.0 ml) and the whole was stirred at 80° C. for 21 hours. After completion of the reaction, the solvent was distilled off. The resultant was added with a saturated aqueous sodium hydrogen carbonate solution and the whole was subjected to extraction with chloroform and dried with magnesium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (37.9 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionThe resultant was added with a saturated aqueous sodium hydrogen carbonate solution
  4. extractionthe whole was subjected to extraction with chloroform
  5. dry with materialdried with magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  8. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-399db86c1863469f93e559d08a3820ea
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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