Triethylamine → HCID 178469058, compound

HRID 488913Notes

Reaction equation

HRID 488913 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[S:5])#[N:2].O=[C:8]([CH2:14][C:15](=O)[CH3:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(N(CC)CC)C>CCO>[CH2:12]([O:11][C:9](=[O:10])[C:8]1[CH:14]=[C:15]([CH3:16])[N:6]=[C:4]([SH:5])[C:3]=1[C:1]#[N:2])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69208Ethyl 2,4-dioxovalerateHCID 14162772-Cyanoethanethioamide

Product 1

HCID 178469058HCID 178469058, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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. filtrationFiltration
  2. washwashing of the
  3. customprecipitates with EtOH

Sources & evidence

ORD record
ord-bb222793f39e44d8b4d1d09a5457a52c
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

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