1H-imidazole-2-carbaldehyde → HCID 67068505, compound

HRID 536103Notes

Reaction equation

HRID 536103 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[CH:9][C:10]=1[NH2:11])=[O:5])[CH3:2].[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH:17]=O.[BH3-]C#N.[Na+]>CO>[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][NH:11][C:10]1[CH:9]=[CH:8][NH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 3

HCID 249551H-imidazole-2-carbaldehydeHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 67068505HCID 67068505, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction mixture with 3-amino-1H-pyrrole-2-carboxylic acid ethyl ester (0.2 g, 1.30 mmol), 2-imidazolecarboxaldehyde (0.15 g, 1.53 mmol), NaCNBH3 (0.082 g, 1.30 mmol) and OHAc (0.15 mL, 2.60 mmol) in methanol (5 mL) was stirred at r.t. for 2 h. The solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate. Washed with water and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried (MgSO4), filtered and concentrated. The crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol), obtaining 0.30 g (99%) of the title compound.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washWashed with water
  4. extractionthe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol)

Sources & evidence

ORD record
ord-3274880faecb411d96e56b5b0484075a
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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