Acetic Acid → (4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-carbamic acid t-butyl ester

HRID 2080711Notes

Reaction equation

HRID 2080711 reaction equation
[C:1]([O:5][C:6](=[O:34])[N:7]([CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][CH2:17][C:18]2[NH:19][CH:20]=[CH:21][N:22]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+].C(O)(=O)C.[CH3:43][N:44]1[CH:48]=[CH:47][N:46]=[C:45]1[CH:49]=O>CO>[C:1]([O:5][C:6](=[O:34])[N:7]([CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32][CH3:33])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]([CH2:17][C:18]2[NH:19][CH:20]=[CH:21][N:22]=2)[CH2:49][C:45]2[N:44]([CH3:43])[CH:48]=[CH:47][N:46]=2)=[CH:13][CH:14]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66941456(4-dipropylaminobutyl)-(4-{[(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)carbamic Acid t-butyl Ester

Product 1

HCID 11592205(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-carbamic acid t-butyl esterYield 71.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (231 mg) obtained in Example 1-6 was dissolved in anhydrous methanol (5.0 ml) The solution was added with sodium cyanoborohydride (61.6 mg), acetic acid (2.00 ml), and 1-methyl-2-imidazole carboxaldehyde (80.9 mg) and the whole was stirred at room temperature for 6 days under a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off. The resultant was then dissolved in chloroform and added with a saturated aqueous sodium hydrogen carbonate solution and the whole was stirred for a while. The solution was subjected to extraction with chloroform and the extract was then washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining the subject compound (197 mg) as a colorless oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe resultant was then dissolved in chloroform
  4. additionadded with a saturated aqueous sodium hydrogen carbonate solution
  5. stirringthe whole was stirred for a while
  6. extractionThe solution was subjected to extraction with chloroform
  7. washthe extract was then washed with a saturated aqueous sodium hydrogen carbonate solution
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. distillationSubsequently, the solvent was distilled off
  10. customthe residue was then purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-72541c2e7eda46848a9f86066148a5d9
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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