ethyl 2-(1H-1,3-benzodiazol-2-yl)acetate → 2-Benzimidazol-2-yl-N-(4-cyano(3-pyridyl))acetamide

HRID 722152Notes

Reaction equation

HRID 722152 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:13][C:12]=1[CH2:20][C:21]([O:23]CC)=O.[NH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[C:33]#[N:34]>C1COCC1>[N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:11][C:12]=1[CH2:20][C:21]([NH:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[C:33]#[N:34])=[O:23]

Participants

5

Reactant 3

HCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 2733832Lithium HexamethyldisilazideHCID 106782193-Aminopyridine-4-carbonitrile

Product 1

HCID 129887822-Benzimidazol-2-yl-N-(4-cyano(3-pyridyl))acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiHMDS (2.5 eq) was added to ethyl 2-benzimidazol-2-ylacetate (1.0 eq) in THF at −78° C. After 1 hour, 3-amino-4-cyanopyridine (0.8 eq) in THF was added. The resulting mixture was allowed to warm to room temperature overnight. The mixture was quenched with NH4Cl (aqueous saturated solution) and extracted with EtOAc. The organic layer washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a brown solid. The crude material was purified by silica gel chromatography (5:1 EtOAc:hexane) to yield the desired product. LC/MS m/z 278.3 (MH+), Rt 1.88 minutes.

Workup

  1. customThe mixture was quenched with NH4Cl (aqueous saturated solution)
  2. extractionextracted with EtOAc
  3. washThe organic layer washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a brown solid
  8. customThe crude material was purified by silica gel chromatography (5:1 EtOAc:hexane)

Sources & evidence

ORD record
ord-07b89cd00263483eac8b4c9e4fd2aedb
Source dataset
uspto-grants-2006_11
Patent number
US07138409B2

Reaction notes

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