2-Bromoacetamide → HCID 11778364, compound

HRID 1063108Notes

Reaction equation

HRID 1063108 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-a61bb737fb0a4720a8fbbac87e1f1e7c
Source dataset
uspto-grants-2005_11
Patent number
US06964956B2

Reaction notes

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