Water → 3-Amino-6-(3,4-dimethoxyphenyl)-4-methyl-thieno[2,3-b]pyridine-2-carboxamide

HRID 556405

Reaction equation

HRID 556405 reaction equation
CC[O-].[Na+].[SH:5][C:6]1[C:11]([C:12]#[N:13])=[C:10]([CH3:14])[CH:9]=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[N:7]=1.Cl[CH2:26][C:27]([NH2:29])=[O:28].O>C(O)C>[NH2:13][C:12]1[C:11]2[C:6](=[N:7][C:8]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)=[CH:9][C:10]=2[CH3:14])[S:5][C:26]=1[C:27]([NH2:29])=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6580ChloroacetamideHCID 2723922Sodium ethoxideHCID 1784885622-Mercapto-6-(3,4-dimethoxyphenyl)-4-methyl-pyridine-3-carbonitrile

Product 1

HCID 575037143-Amino-6-(3,4-dimethoxyphenyl)-4-methyl-thieno[2,3-b]pyridine-2-carboxamideYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.1 g (31.4 mmol) sodium ethylate are dissolved in 40 ml absolute ethanol. 3.0 g (10.5 mmol) 2-mercapto-6-(3,4-dimethoxyphenyl)-4-methyl-pyridine-3-carbonitrile and 1.2 g (12.6 mmol) 2-chloroacetamide are added and refluxed for 1 h. Following cooling, 10 ml water are added and the precipitate is sucked off, suck dried and dried in vacuo at 50° C. 3.4 g (94%) 3-amino-6-(3,4-dimethoxyphenyl)-4-methyl-thieno[2,3-b]-pyridine-2-carboxamide is obtained.

Workup

  1. temperaturerefluxed for 1 h
  2. temperatureFollowing cooling
  3. customsuck dried
  4. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-cc6d5dd4b1c04f09a1b1427ba0e48989
Source dataset
uspto-grants-2011_11
Patent number
US08058285B2

Linked notes

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