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Triethylamine → 4-{[bis(1-heptyloxycarbonyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethylphenyl)-benzamide

HRID 348697
Notes
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Reaction equation

HRID 348697 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:37]=[CH:36][C:18]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][N:29]([CH2:33][CH2:34][CH3:35])[CH2:30][CH2:31][CH3:32])=[CH:24][CH:23]=2)=[O:20])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.C(N([CH2:43][CH3:44])CC)C.Cl[C:46]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[O:47].[C:56](=[O:59])(O)[O-:57].[Na+]>ClCCl>[CH2:49]([O:48][C:46]([N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:37]=[CH:36][C:18]([C:19]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][N:29]([CH2:33][CH2:34][CH3:35])[CH2:30][CH2:31][CH3:32])=[CH:26][CH:27]=2)=[O:20])=[CH:17][CH:16]=1)[CH2:8][C:9]1[N:13]([C:56]([O:57][CH2:17][CH2:16][CH2:15][CH2:37][CH2:36][CH2:43][CH3:44])=[O:59])[CH:12]=[CH:11][N:10]=1)=[O:47])[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 118547Carbonochloridic acid, heptyl esterHCID 516892Sodium BicarbonateHCID 99834204-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethylphenyl)-benzamide

Product 1

HCID 588019204-{[bis(1-heptyloxycarbonyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethylphenyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (83.8 mg) obtained in Example 19-3 was dissolved in anhydrous dichloromethane (1.5 ml). The solution was added with triethylamine (70.1 μl) and then added with n-heptyl chloroformate (74.9 μl) in an ice bath, followed by stirring overnight under a nitrogen atmosphere at room temperature. After completion of the reaction, the solution was added with a saturated aqueous sodium bicarbonate solution and stirred for a while. Then, the solution was extracted with chloroform and washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (111 mg) as a brown solid.

Workup

  1. customAfter completion of the reaction
  2. stirringstirred for a while
  3. extractionThen, the solution was extracted with chloroform
  4. washwashed with a saturated aqueous sodium bicarbonate solution and saturated saline solution
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. distillationSubsequently, the solvent was distilled off
  7. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-56b41646f9ac4e79b279101003e3eaab
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07176227B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes