4-Toluenesulfonyl chloride → 4-({bis[1-(toluene-4-sulfonyl)-1H-imidazol-2-ylmethyl]-amino}-methyl)-N-(4-dipropylaminomethylphenyl)-benzamide

HRID 348663Notes

Reaction equation

HRID 348663 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.[C:45]1([CH3:55])[CH:50]=[CH:49][C:48]([S:51](Cl)(=[O:53])=[O:52])=[CH:47][CH:46]=1>C(Cl)(Cl)Cl>[C:43]1([CH3:44])[CH:50]=[CH:49][C:48]([S:51]([N:1]2[CH:5]=[CH:4][N:3]=[C:2]2[CH2:6][N:7]([CH2:14][C:15]2[CH:37]=[CH:36][C:18]([C:19]([NH:21][C:22]3[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]=3)=[O:20])=[CH:17][CH:16]=2)[CH2:8][C:9]2[N:13]([S:51]([C:48]3[CH:49]=[CH:50][C:45]([CH3:55])=[CH:46][CH:47]=3)(=[O:53])=[O:52])[CH:12]=[CH:11][N:10]=2)(=[O:53])=[O:52])=[CH:47][CH:46]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 99834204-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminomethylphenyl)-benzamide

Product 1

HCID 588018944-({bis[1-(toluene-4-sulfonyl)-1H-imidazol-2-ylmethyl]-amino}-methyl)-N-(4-dipropylaminomethylphenyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The compound (50.8 mg) obtained in Example 19-3 was dissolved in anhydrous chloroform (2.0 ml). The solution was added with triethylamine (0.049 ml) and then added with p-toluenesulfonyl chloride (manufactured by Kanto Kagaku) (57.2 mg), followed by stirring at room temperature for 16 hours. After completion of the reaction, chloroform (3.0 ml) was added to the solution, and the whole was washed with water. The organic layer was dried with anhydrous magnesium sulfate. Subsequently, the solvent was distilled off and the residue was then purified through silica gel column chromatography (manufactured by Fuji Silysia Chemical Ltd.) (hexane/ethyl acetate), thereby obtaining the subject compound (15.2 mg) as a white solid.

Workup

  1. additionwas added to the solution
  2. washthe whole was washed with water
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. distillationSubsequently, the solvent was distilled off
  5. customthe residue was then purified through silica gel column chromatography (manufactured by Fuji Silysia Chemical Ltd.) (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-297cfc6efa0c4f58a6f02d6001fd5a6b
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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