2-Bromoacetamide → HCID 11778364, compound

HRID 750735Notes

Reaction equation

HRID 750735 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-51214cd510f54fd48666d5010c65d086
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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