Trimethyl orthoformate → HCID 63292554, compound

HRID 2080881Notes

Reaction equation

HRID 2080881 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][NH2:8].C(OC)(OC)OC.[NH:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH:21]=O.[BH4-].[Na+]>CO>[NH:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH2:21][NH:8][CH2:7][C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 533842(1-methyl-1H-imidazol-2-yl)methanamineHCID 4311764Sodium borohydride

Product 1

HCID 63292554HCID 63292554, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (201 mg) obtained in Example 14-7 was dissolved in methanol (4.0 ml) and added with trimethyl orthoformate (200 μl) and 2-imidazole carboxaldehyde (115 mg) and the whole was stirred at room temperature for 30 minutes. After having been cooled to 0° C., the solution was added with sodium borohydride (89.6 mg) and then the whole was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and washed with water, followed by 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 under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (137 mg) as a pale-yellow oily substance.

Workup

  1. temperatureAfter having been cooled to 0° C.
  2. stirringthe whole was stirred at room temperature for 1 hour
  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 water
  7. extractionfollowed by extraction with chloroform
  8. washThe organic layer was washed with a 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/methanol)

Sources & evidence

ORD record
ord-b52a458005b6482ea9a3cd023a618e3e
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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