2-Bromoacetamide → HCID 11778364, compound

HRID 488914Notes

Reaction equation

HRID 488914 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([SH:12])[C:6]=1[C:13]#[N:14])[CH3:2].Br[CH2:17][C:18]([NH2:20])=[O:19].[O-]CC.[Na+]>CO>[CH2:1]([O:3][C:4]([C:5]1[C:6]2[C:13]([NH2:14])=[C:17]([C:18](=[O:19])[NH2:20])[S:12][C:7]=2[N:8]=[C:9]([CH3:11])[CH:10]=1)=[O:15])[CH3:2]

Participants

5

Reactant 3

HCID 696322-BromoacetamideHCID 2723922Sodium ethoxideHCID 178469058HCID 178469058, compound

Product 1

HCID 11778364HCID 11778364, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-cyanothioacetamide (3.52 g, 35 mmol) and ethyl 2,4-dioxovalerate (5.0 g, 32 mmol) in anhydrous EtOH (75 mL) at room temperature was added triethylamine (0.5 mL) and the reaction was stirred overnight. Filtration and washing of the precipitates with EtOH gave 3-cyano-2-mercapto-6-methyl-isonicotinic acid ethyl ester as a yellow solid (4.54 g, 64.5%). A mixture of this ester (3.54 g, 16 mmol), bromoacetamide (2.15 g, 16 mmol) and sodium ethoxide (2.18 g, 32 mmol) in MeOH was heated at reflux overnight. It was then allowed to cool to room temperature. Filtration and washing of the precipitates with EtOH provided 3-amino-2-carbamoyl-6-methyl-thieno[2,3-b]pyridine-4-carboxylic acid ethyl ester as a solid (0.94 g, 21.1%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationFiltration
  4. washwashing of the
  5. customprecipitates with EtOH

Sources & evidence

ORD record
ord-52e307143c4140d497be0a5192124438
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

Loading…