Trimethyl orthoformate → 2-{[(1H-imidazol-2-ylmethyl)amino]methyl}-6-(4-dipropylaminobutyl)naphthalene

HRID 348751Notes

Reaction equation

HRID 348751 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:9]=2)[CH:4]=1.C(OC)(OC)OC.[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH:36]=O.[BH4-].[Na+].[Cl-].[NH4+]>CO>[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH2:36][NH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:9]=2)[CH:4]=1

Participants

7

Reactant 5

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 210843902-Aminomethyl-6-(4-dipropylaminobutyl)naphthalene

Product 1

HCID 210843702-{[(1H-imidazol-2-ylmethyl)amino]methyl}-6-(4-dipropylaminobutyl)naphthaleneYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (67.5 mg) obtained in Example 124-4 was dissolved in anhydrous methanol (2.0 ml) and added with trimethyl orthoformate (0.0354 ml) and 2-imidazole carboxaldehyde (20.8 mg), followed by stirring at room temperature for 2 hours under a nitrogen atmosphere. Subsequently, the solution was added with sodium borohydride (12.3 mg) in an ice bath and then stirred at room temperature for 1 hour. After completion of the reaction, a saturated aqueous ammonium chloride solution was added to the solution, and the whole was stirred. The solution was subjected to extraction with chloroform and the extract was then washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (39.0 mg) as a yellow oily substance.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customAfter completion of the reaction
  3. stirringthe whole was stirred
  4. extractionThe solution was subjected to extraction with chloroform
  5. washthe extract was then washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was then purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-6179054956224b98afa67848c9dcfb52
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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