Acetic Acid → Ethyl 3-{[(4,5-dimethyl-1H-benzimidazol-2-yl)methyl]amino}-1H-pyrrole-2-carboxylate

HRID 536108Notes

Reaction equation

HRID 536108 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].[CH3:12][C:13]1[C:21]2[N:20]=[C:19]([CH:22]=O)[NH:18][C:17]=2[CH:16]=[CH:15][C:14]=1[CH3:24].CC(O)=O.[BH3-]C#N.[Na+].[OH-].[Na+]>CO>[CH3:12][C:13]1[C:21]2[N:20]=[C:19]([CH2:22][NH:11][C:10]3[CH:9]=[CH:8][NH:7][C:6]=3[C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:18][C:17]=2[CH:16]=[CH:15][C:14]=1[CH3:24]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 451207614,5-Dimethyl-1H-benzo[d]imidazole-2-carbaldehyde

Product 1

HCID 67068491Ethyl 3-{[(4,5-dimethyl-1H-benzimidazol-2-yl)methyl]amino}-1H-pyrrole-2-carboxylateYield 27.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Amino-1H-pyrrole-2-carboxylic acid ethyl ester (0.077 g, 0.5 mmol), 4,5-dimethyl-1H-benzimidazole-2-carbaldehyde (0.130 g, 0.75 mmol) and HOAc (0.045 g, 0.75 mmol) were stirred in methanol (4 mL) followed by addition of NaCNBH3. The resulting mixture was stirred at r.t. for 16 h. The reaction mixture was neutralized with 2M NaOH and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate and extracted with water. The organic layer was dried (Na2SO4) and concentrated. The crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 100% ethyl acetate), obtaining a white solid, 0.043 g (27%) of the title compound, as a tautomeric mixture (1:1).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. extractionextracted with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 100% ethyl acetate)

Sources & evidence

ORD record
ord-68ea19a65e0c48b19874fe27ea10611a
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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