1-Methyl-2-imidazolecarboxaldehyde → HCID 11719896, compound

HRID 2080809Notes

Reaction equation

HRID 2080809 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][N:13]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:12]2.[CH3:29][N:30]1[CH:34]=[CH:33][N:32]=[C:31]1[CH:35]=O.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.C(O)(=O)C>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][N:13]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:23][CH2:24][CH3:25])[CH2:26][CH2:27][CH3:28])[CH2:12]2)[CH2:35][C:31]1[N:30]([CH3:29])[CH:34]=[CH:33][N:32]=1

Participants

7

Reactant 4

HCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 23155408HCID 23155408, compound

Product 1

HCID 11719896HCID 11719896, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The compound (12.5 mg) obtained in Example 38-1 was dissolved in methanol (2.0 ml) and added with 1-methyl-2-imidazole carboxaldehyde (4.4 mg) and sodium cyanoborohydride (4.2 mg). The solution was adjusted to pH 4 with acetic acid and stirred at room temperature for 8 hours. The residue obtained by concentration of the solution was added with a saturated aqueous sodium hydrogen carbonate solution to neutralize the solution and the whole was subjected to extraction with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and dried with anhydrous sodium sulfate. The residue obtained by distilling the solvent off was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (7.7 mg) as a colorless oily substance.

Workup

  1. customThe residue obtained by concentration of the solution
  2. extractionthe whole was subjected to extraction with chloroform
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. distillationby distilling the solvent
  7. customoff was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-ee9ee76c81504fc7a83ee50ec53db27c
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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