Acetic Acid → N-[4-(cyclohexylamino)butyl]-4-[[1H-imidazol-2-ylmethyl-[(1-methylimidazol-2-yl)methyl]amino]methyl]benzenesulfonamide

HRID 348705Notes

Reaction equation

HRID 348705 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:25][C:26]2[NH:27][CH:28]=[CH:29][N:30]=2)[CH2:18][C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8].[C:31]1(=O)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH:31]1([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:25][C:26]3[NH:30][CH:29]=[CH:28][N:27]=3)[CH2:18][C:19]3[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=3)=[CH:12][CH:11]=2)(=[O:8])=[O:9])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 66941735HCID 66941735, compound

Product 1

HCID 58801913N-[4-(cyclohexylamino)butyl]-4-[[1H-imidazol-2-ylmethyl-[(1-methylimidazol-2-yl)methyl]amino]methyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (173.5 mg) obtained in Example 102-4 was dissolved in anhydrous methanol (7.0 ml). Then, the solution was added with cyclohexanone (0.083 ml) and sodium cyanoborohydride (75.4 mg) and adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 16.5 hours. After the reaction, the solvent was distilled off. Subsequently, the residue was added with a 1 mol/l sodium hydroxide aqueous solution (7.0 ml), followed by extraction with chloroform. The extract was dried with magnesium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/methanol) and then treated with hydrochloric acid, thereby obtaining hydrochloride (161.6 mg) of the subject compound as a white solid.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off
  3. additionSubsequently, the residue was added with a 1 mol/l sodium hydroxide aqueous solution (7.0 ml)
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe extract was dried with magnesium sulfate
  6. distillationthe solvent was then distilled off
  7. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  8. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-4d62bd7f343b4820af12617605cc63cb
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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