Triethylamine → Hexyl 2-[[[4-[[4-[(dipropylamino)methyl]phenyl]carbamoyl]phenyl]methyl-[(1-hexoxycarbonylimidazol-2-yl)methyl]amino]methyl]imidazole-1-carboxylate

HRID 348696Notes

Reaction equation

HRID 348696 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.Cl[C:39]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[O:40].C(N([CH2:53][CH3:54])CC)C>C(Cl)(Cl)Cl>[CH2:42]([O:41][C:39]([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:39]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:53][CH3:54])=[O:40])[CH:12]=[CH:11][N:10]=1)=[O:40])[CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22466Hexyl chloroformateHCID 99834204-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethylphenyl)-benzamide

Product 1

HCID 58801928Hexyl 2-[[[4-[[4-[(dipropylamino)methyl]phenyl]carbamoyl]phenyl]methyl-[(1-hexoxycarbonylimidazol-2-yl)methyl]amino]methyl]imidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The compound obtained in Example 19-3 was treated with an anion-exchange resin. The treated product was dissolved in chloroform (4.0 ml) and added with n-hexyl chloroformate (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (0.054 ml) and triethylamine (0.060 ml), followed by stirring at room temperature for 16 hours. After completion of the reaction, the solvent was distilled off. The residue was added with chloroform, washed with water and saturated saline solution, and dried with anhydrous sodium sulfate, followed by distilling the solvent off. Subsequently, the residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (66.6 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionThe residue was added with chloroform
  4. washwashed with water and saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationby distilling the solvent off
  7. customSubsequently, the residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-8e4fce9351804670beee69cf915a10f1
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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