Acetic Acid → Ethyl 3-[(1H-benzimidazol-2-ylmethyl)amino]-1H-pyrrole-2-carboxylate

HRID 1171784Notes

Reaction equation

HRID 1171784 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[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH:21]=O.[BH3-]C#N.[Na+].CC(O)=O>CO>[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH2:21][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

6

Reactant 4

HCID 176Acetic AcidHCID 768261H-Benzimidazole-2-carboxaldehydeHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 67068526Ethyl 3-[(1H-benzimidazol-2-ylmethyl)amino]-1H-pyrrole-2-carboxylateYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction mixture of 3-amino-1H-pyrrole-2-carboxylic acid ethyl ester (0.77 g, 4.99 mmol), 1H-benzoimidazole-2-carboxaldehyde (0.88 g, 5.99 mmol), NaCNBH3 (0.31 g, 4.99 mmol) and HOAc (0.57 mL, 9.99 mmol) in methanol (15 mL) was stirred at r.t. overnight. The mixture was then heated at 50° C. for 5 h. Cooled to r.t. and evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with water. The aqueous phase was extracted with ethyl acetate (twice). The combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography (heptane/ethyl acetate (1:0 to 0:1), obtaining 1.15 g (81%) of the title compound.

Workup

  1. temperatureThe mixture was then heated at 50° C. for 5 h
  2. temperatureCooled to r.t.
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. extractionThe aqueous phase was extracted with ethyl acetate (twice)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude product was purified by flash column chromatography (heptane/ethyl acetate (1:0 to 0:1)

Sources & evidence

ORD record
ord-e358cd2e12844b23aae0c5f978d07c39
Source dataset
uspto-grants-2010_11
Patent number
US07829707B2

Reaction notes

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