Triethylamine → HCID 178469058, compound

HRID 750734Notes

Reaction equation

HRID 750734 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-4b1c384e43ef414db4fc56aafcf44697
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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