1H-imidazole-2-carbaldehyde → HCID 67103762, compound

HRID 2080875Notes

Reaction equation

HRID 2080875 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[C:15]1[CH:19]=O.[BH4-].[Na+].[CH3:23][N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[CH:29]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:11][O:10][C:8](=[O:9])[C:7]1[CH:6]=[CH:5][C:4]([CH2:3][N:2]([CH2:19][C:15]2[NH:14][CH:18]=[CH:17][N:16]=2)[CH2:29][C:25]2[N:24]([CH3:23])[CH:28]=[CH:27][N:26]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 249551H-imidazole-2-carbaldehydeHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 4311764Sodium borohydrideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67103762HCID 67103762, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Commercially available methyl 4-aminomethyl-benzoate hydrochloride was subjected to desalting, thereby obtaining a free compound. The resultant free compound (1.04 g) was dissolved in methanol (15.0 ml) and added with 2-imidazole carboxaldehyde (0.529 g), and the whole was stirred at room temperature for 14 hours. After having been cooled to 0° C., the solution was added with sodium borohydride (0.249 g) and the whole was stirred at 0° C. for 30 minutes and then at room temperature for 30 minutes. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution, followed by extraction with chloroform. The extract was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off, thereby obtaining a crude product (1.47 g) of 4-[[(1H-imidazol-2-ylmethyl)-amino]-methyl]-benzoic acid methyl ester. The resultant crude product (1.47 g) was dissolved in methanol (15.0 ml) and added with 1-methyl-2-imidazole carboxaldehyde (0.844 g) and the whole was stirred at room temperature for 1 hour. After having been cooled to 0° C., the solution was added with sodium triacetoxyborohydride (2.18 g) and then the whole was stirred at room temperature for 22 hours. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution. After extraction with chloroform, the organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (1.44 g) as white foam.

Workup

  1. customthereby obtaining a free compound
  2. temperatureAfter having been cooled to 0° C.
  3. stirringthe whole was stirred at 0° C. for 30 minutes
  4. waitat room temperature for 30 minutes
  5. customAfter completion of the reaction
  6. distillationthe solvent was distilled off
  7. dissolutionThe residue was dissolved in chloroform
  8. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  9. extractionfollowed by extraction with chloroform
  10. washThe extract was washed with a saturated saline solution
  11. dry with materialdried with anhydrous sodium sulfate
  12. filtrationAfter filtration
  13. distillationthe solvent was distilled off
  14. customobtaining a crude product (1.47 g) of 4-[[(1H-imidazol-2-ylmethyl)-amino]-methyl]-benzoic acid methyl ester
  15. stirringthe whole was stirred at room temperature for 1 hour
  16. temperatureAfter having been cooled to 0° C.
  17. stirringthe whole was stirred at room temperature for 22 hours
  18. customAfter completion of the reaction
  19. distillationthe solvent was distilled off
  20. dissolutionThe residue was dissolved in chloroform
  21. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  22. extractionAfter extraction with chloroform
  23. washthe organic layer was washed with a saturated saline solution
  24. dry with materialdried with anhydrous sodium sulfate
  25. filtrationAfter filtration
  26. distillationthe solvent was distilled off
  27. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-64bda3f0902a47438789fbdc36c6fc3c
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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