Trimethyl orthoformate → N-(4-dipropylaminomethylbenzyl)-N'-(1H-imidazol-2-ylmethyl)-N'-(1-methyl-1H-imidazol-2-ylmethyl)-1,4-butanediamine

HRID 348721Notes

Reaction equation

HRID 348721 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:13][C:14]1[N:15]([CH3:19])[CH:16]=[CH:17][N:18]=1)[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12].[CH2:20]([N:23]([CH2:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)[CH2:24][CH2:25][CH3:26])[CH2:21][CH3:22].C(OC)(OC)OC.[BH4-].[Na+]>CO>[CH2:20]([N:23]([CH2:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:12][CH2:11][CH2:10][CH2:9][CH2:8][N:7]([CH2:6][C:2]2[NH:1][CH:5]=[CH:4][N:3]=2)[CH2:13][C:14]2[N:15]([CH3:19])[CH:16]=[CH:17][N:18]=2)=[CH:30][CH:29]=1)[CH2:24][CH2:25][CH3:26])[CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 4311764Sodium borohydrideHCID 130230014-((Dipropylamino)methyl)benzaldehydeHCID 66941777N-(1H-imidazol-2-ylmethyl)-N-(1-methyl-1H-imidazol-2-ylmethyl)butane-1,4-diamine

Product 1

HCID 58801886N-(4-dipropylaminomethylbenzyl)-N'-(1H-imidazol-2-ylmethyl)-N'-(1-methyl-1H-imidazol-2-ylmethyl)-1,4-butanediamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (349 mg) obtained in Example 117-4 was dissolved in methanol (7.0 ml). Then, the solution was added with the compound (323 mg) obtained in Example 117-1 and trimethyl orthoformate (0.340 ml) and stirred at room temperature for 2 hours, followed by cooling to 0° C. The solution was added with sodium borohydride (75.5 mg) and stirred at room temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and washed with an aqueous sodium bicarbonate solution, followed by extraction with chloroform. The organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (chloroform) and treated with hydrochloric acid, thereby obtaining hydrochloride (89.8 mg) of the subject compound as a white solid.

Workup

  1. temperatureby cooling to 0° C
  2. stirringstirred at room temperature for 30 minutes
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionThe residue was dissolved in chloroform
  6. washwashed with an aqueous sodium bicarbonate solution
  7. extractionfollowed by extraction with chloroform
  8. washThe organic layer was washed with saturated saline solution
  9. dry with materialdried with anhydrous sodium sulfate
  10. filtrationAfter filtration
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe residue was purified through silica gel column chromatography (chloroform)
  13. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-0c2e620c84be472994ce3e3967652cdf
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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