ethyl 2-(1H-1,3-benzodiazol-2-yl)acetate → 4-Amino-5-(1H-benzimidazol-2-yl)thieno[2,3-b]pyridin-6(7H)-one

HRID 1882899Notes

Reaction equation

HRID 1882899 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[CH2:20][C:21]([O:23]CC)=O.[NH2:26][C:27]1[S:28][CH:29]=[CH:30][C:31]=1[C:32]#[N:33]>C1COCC1>[NH2:33][C:32]1[C:31]2[CH:30]=[CH:29][S:28][C:27]=2[NH:26][C:21](=[O:23])[C:20]=1[C:12]1[NH:11][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=1

Participants

5

Reactant 3

HCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 7366072-Aminothiophene-3-carbonitrileHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 1358393724-Amino-5-(1H-benzimidazol-2-yl)thieno[2,3-b]pyridin-6(7H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiHMDS (4.3 eq) was added to ethyl 1H-benzimidazol-2-ylacetate (1.1 eq) and 2-aminothiophene-3-carbonitrile (1.0 eq) in THF at 0° C. After 1 hour, the resulting mixture was warmed to room temperature and then stirred overnight. The mixture was quenched with an aqueous saturated NH4Cl solution and extracted with EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a brown solid. LC/MS m/z 283.1 (MH+), Rt 1.88 minutes.

Workup

  1. customThe mixture was quenched with an aqueous saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a brown solid

Sources & evidence

ORD record
ord-93bb75530fde471d8033048a189de96b
Source dataset
uspto-grants-2004_07
Patent number
US06759417B2

Reaction notes

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