2-Bromoacetamide → 3-Amino-6-isobutyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid amide

HRID 750732Notes

Reaction equation

HRID 750732 reaction equation
[CH2:1]([C:5]1[CH:12]=[C:11]([CH3:13])[C:8]([C:9]#[N:10])=[C:7]([SH:14])[N:6]=1)[CH:2]([CH3:4])[CH3:3].Br[CH2:16][C:17]([NH2:19])=[O:18].[O-]CC.[Na+]>CN(C=O)C.O>[NH2:10][C:9]1[C:8]2[C:7](=[N:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:12][C:11]=2[CH3:13])[S:14][C:16]=1[C:17]([NH2:19])=[O:18]

Participants

6

Reactant 3

HCID 696322-BromoacetamideHCID 2723922Sodium ethoxideHCID 178425008HCID 178425008, compound

Product 1

HCID 100384143-Amino-6-isobutyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of the above nitrile (1.00 g, 4.85 mmol), bromoacetamide (0.67 g, 4.85 mmol), and sodium ethoxide (0.68 g, 10 mmol) in DMF (20 mL) was heated at 70° C. for 1 h before it was allowed to cool to room temperature. The resulting mixture was diluted with water, filtrated and the precipitates washed with EtOH providing the title compound (0.5 g, 39%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltrated
  3. washthe precipitates washed with EtOH providing the title compound (0.5 g, 39%)

Sources & evidence

ORD record
ord-16c495119dd044ff98f63fc3cd7a90a1
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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