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

HRID 2080861
Notes
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Reaction equation

HRID 2080861 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].C(Cl)(Cl)Cl.[CH2:43]([OH:49])[CH2:44][O:45][CH2:46][CH2:47]O>>[OH:49][CH2:43][CH2:44][O:45][CH2:46][CH2:47][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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 6212ChloroformHCID 8117Diethylene GlycolHCID 11540944[(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid

Product 1

HCID 11512812[(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-amino]-acetic acid-2-(2-hydroxy-ethoxy)-ethyl ester

Conditions

Temperature
80 °C

Procedure

The compound (424.0 mg) obtained in Example 65-1 was dissolved in diethylene glycol (8.0 ml) and the whole was stirred at 80° C. for 3 days. After completion of the reaction, the resultant was added with chloroform and washed with water, followed by drying with magnesium 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 (280.2 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. washwashed with water
  3. dry with materialby drying with magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  6. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-83f5467836ac4630a62f4da896762a9e
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932281B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes