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

HRID 1173950Notes

Reaction equation

HRID 1173950 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][CH3:52])=[O:47]>C(Cl)(Cl)Cl>[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:46]([O:48][CH2:49][CH2:50][CH2:43][CH3:44])=[O:47])[CH:12]=[CH:11][N:10]=1)=[O:47])[CH2:50][CH2:51][CH3:52]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 99834204-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethylphenyl)-benzamide

Product 1

HCID 588019074-{[bis(1-butoxycarbonyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethylphenyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The compound obtained in Example 19-3 was treated with an anion-exchange resin and then dissolved in anhydrous chloroform (2.8 ml). Subsequently, the solution was added with triethylamine (0.059 ml) and n-butyl chloroformate (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (0.044 ml), followed by stirring at room temperature for 17.5 hours. After completion of the reaction, the solution was added with chloroform (3.0 ml), washed with water, and dried with anhydrous magnesium sulfate, followed by distilling the solvent off. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (66.9 mg) as a brown viscous substance.

Workup

  1. customAfter completion of the reaction
  2. washwashed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationby distilling the solvent off
  5. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-61b27c46521c4dc79c2e08b352121f19
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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