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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe mixture was then heated at 50° C. for 5 h
- temperatureCooled to r.t.
- customevaporated in vacuo
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with water
- extractionThe aqueous phase was extracted with ethyl acetate (twice)
- dry with materialThe combined organic layers were dried (MgSO4)
- concentrationconcentrated
- customThe crude product was purified by flash column chromatography (heptane/ethyl acetate (1:0 to 0:1)
Sources & evidence
- ORD record
- ord-6b5f3f91fcb74e599bb6787659d0c083
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859568B2
Linked notes
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