2-Bromoacetamide → 3-Amino-4,6-dimethylthieno(2,3-b)pyridine-2-carboxamide

HRID 750741Notes

Reaction equation

HRID 750741 reaction equation
Br[CH2:2][C:3]([NH2:5])=[O:4].[SH:6][C:7]1[N:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:8]=1[C:9]#[N:10].C[O-].[Na+]>CO>[NH2:10][C:9]1[C:8]2[C:7](=[N:14][C:13]([CH3:15])=[CH:12][C:11]=2[CH3:16])[S:6][C:2]=1[C:3]([NH2:5])=[O:4]

Participants

5

Reactant 3

HCID 696322-BromoacetamideHCID 10942334Sodium MethoxideHCID 178425247HCID 178425247, compound

Product 1

HCID 6135283-Amino-4,6-dimethylthieno(2,3-b)pyridine-2-carboxamideYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

α-Bromoacetamide (388 mg, 2.81 mmol) was added to a solution of 2-mercapto-4,6-dimethyl-nicotinonitrile (420 mg, 2.56 mmol) in MeOH (25 mL) at room temperature. This was followed by addition of sodium methoxide (1.76 mL, 25% NaOMe in MeOH, 7.7 mmol). The reaction mixture was heated to reflux. Heating at reflux was continued overnight, after which time the reaction mixture was cooled and filtered. The product was dried overnight providing 450 mg (80%) of the title compound, m.p. 238-40° C.

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. temperatureHeating
  3. temperatureat reflux
  4. temperatureafter which time the reaction mixture was cooled
  5. filtrationfiltered
  6. customThe product was dried overnight

Sources & evidence

ORD record
ord-bfa107bc8670466f97ad0afd21d1f8ef
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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