Sodium Hydroxide → N-[4-[(dipropylamino)methyl]phenyl]-4-[[(1-ethylimidazol-2-yl)methyl-(1H-imidazol-2-ylmethyl)amino]methyl]benzamide

HRID 348690Notes

Reaction equation

HRID 348690 reaction equation
C(N(CCC)[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:27])[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:20][CH2:21][C:22]3[NH:23][CH:24]=[CH:25][N:26]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)CC.[CH2:31]([N:33]1[CH:37]=[CH:36][N:35]=[C:34]1[CH:38]=O)[CH3:32].[C:40]([BH3-])#[N:41].[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH2:6]([N:41]([CH2:40][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:27])[C:13]2[CH:14]=[CH:15][C:16]([CH2:19][N:20]([CH2:38][C:34]3[N:33]([CH2:31][CH3:32])[CH:37]=[CH:36][N:35]=3)[CH2:21][C:22]3[NH:26][CH:25]=[CH:24][N:23]=3)=[CH:17][CH:18]=2)=[CH:9][CH:10]=1)[CH2:7][CH2:8][CH3:9])[CH2:5][CH3:10]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 110623771-ethyl-1H-imidazole-2-carbaldehydeHCID 21084514N-[4-(dipropylamino)phenyl]-4-[(1H-imidazol-2-ylmethylamino)methyl]benzamide

Product 1

HCID 49771572N-[4-[(dipropylamino)methyl]phenyl]-4-[[(1-ethylimidazol-2-yl)methyl-(1H-imidazol-2-ylmethyl)amino]methyl]benzamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The compound (120 mg) obtained in Example 47-3 was dissolved in methanol (5.0 ml) and then added with the compound (58.0 mg) obtained in Example 90-1 and sodium cyanoborohydride (18.0 mg). Then, the solution was adjusted to pH 5 with acetic acid and then stirred at room temperature for 2 days. After completion of the reaction, a 1 mol/l sodium hydroxide aqueous solution was added to the reaction solution, followed by separation/extraction with chloroform. The organic layer was dried with anhydrous sodium 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 (107 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by separation/extraction with chloroform
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. distillationthe solvent was then distilled off
  5. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  6. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-cfad80e99b074f4abf711c1707994045
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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