Hydrogen Peroxide → 3-Amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

HRID 656640Notes

Reaction equation

HRID 656640 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[S:19][C:10]3=[N:11][C:12]([S:17][CH3:18])=[C:13]([Cl:16])[C:14]([CH3:15])=[C:9]3[C:8]=2[NH2:20])=[O:6])[CH2:3][CH2:2]1.[OH:21]O.O>C(O)(=O)C>[CH:1]1([NH:4][C:5]([C:7]2[S:19][C:10]3=[N:11][C:12]([S:17]([CH3:18])=[O:21])=[C:13]([Cl:16])[C:14]([CH3:15])=[C:9]3[C:8]=2[NH2:20])=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962Water2×HCID 576644033-Amino-5-chloro-4-methyl-6-methylsulfanyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

Product 1

HCID 576644203-Amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamideYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
35 °C

Procedure

To a slurry of 3-amino-5-chloro-4-methyl-6-methylsulfanyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide (7.5 g, 22.87 mmol) in glacial acetic acid (75 ml) is added a solution of 30% hydrogen peroxide in water (2.85 ml, 25.16 mmol). The mixture is stirred at 35° C. for 16 hour, cooled to room temperature, and poured over water (300 ml). A bright yellow precipitate is formed. The mixture is stirred at 0° C. for 1 hour then the solid is collected by filtration and dried under vacuum at 60° C. for 3 hours to afford the title compound as a bright yellow solid (5.58 g, 71%). Mass (m/z): 344.1 (M++1).

Workup

  1. temperaturecooled to room temperature
  2. customA bright yellow precipitate is formed
  3. stirringThe mixture is stirred at 0° C. for 1 hour
  4. filtrationthe solid is collected by filtration
  5. customdried under vacuum at 60° C. for 3 hours

Sources & evidence

ORD record
ord-ae987ebe6e8b43cfa8f88872af2103dd
Source dataset
uspto-grants-2011_12
Patent number
US08071776B2

Reaction notes

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