Trimethyl orthoformate → 6-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amide

HRID 2080775Notes

Reaction equation

HRID 2080775 reaction equation
[CH2:1]([N:4]([CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]1[N:13]=[C:14]2[CH2:19][CH2:18][CH:17]([CH2:20][NH2:21])[CH2:16][N:15]2[CH:22]=1)=[O:11])[CH2:2][CH3:3].C(OC)(OC)OC.[NH:33]1[CH:37]=[CH:36][N:35]=[C:34]1[CH:38]=O.[BH4-].[Na+]>CO.O>[CH2:23]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]1[N:13]=[C:14]2[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][CH2:38][C:34]3[NH:33][CH:37]=[CH:36][N:35]=3)[CH2:16][N:15]2[CH:22]=1)=[O:11])[CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 231556046-Aminomethyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amide

Product 1

HCID 231554046-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid-(4-dipropylamino-butyl)-amideYield 87.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The compound (28.3 mg) obtained in Example 19-3 was dissolved in methanol (1.0 ml) and added with trimethyl orthoformate (0.030 ml) and 2-imidazole carboxaldehyde (11.7 mg), and the whole was stirred at room temperature for 3 hours. After having been cooled to 0° C., the solution was added with sodium borohydride (4.6 mg) and the whole was warmed to room temperature and stirred for additional 15 minutes. The resultant was added with water to stop the reaction and subjected to extraction with chloroform. The organic layer was washed with water and a saturated saline solution and dried with anhydrous sodium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (30.5 mg) as a colorless oily substance.

Workup

  1. temperatureAfter having been cooled to 0° C.
  2. temperaturethe whole was warmed to room temperature
  3. stirringstirred for additional 15 minutes
  4. customthe reaction
  5. extractionsubjected to extraction with chloroform
  6. washThe organic layer was washed with water
  7. dry with materiala saturated saline solution and dried with anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-5d6836160df14b33ae55871932daac39
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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