Hydrochloric Acid → HCID 19347984, compound

HRID 1637207Notes

Reaction equation

HRID 1637207 reaction equation
[OH:1]O.O.[N:4]1([CH2:13][C:14]2[CH:15]=[CH:16][C:17]3[C:21]([S:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)=[C:20]([C:31]([OH:33])=[O:32])[S:19][C:18]=3[CH:34]=2)[C:12]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[N:6]=[CH:5]1.Cl>C(O)(=O)C>[N:4]1([CH2:13][C:14]2[CH:15]=[CH:16][C:17]3[C:21]([S:22]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)=[O:1])=[C:20]([C:31]([OH:33])=[O:32])[S:19][C:18]=3[CH:34]=2)[C:12]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[N:6]=[CH:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 19348002HCID 19348002, compound

Product 1

HCID 19347984HCID 19347984, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Hydrogen peroxide in water (0.07 ml of 30% w/v, 0.58 mmol) was added to a mixture of 6-(1H-Imidazo[4,5-c]pyridin-1-ylmethyl)-3-[(3-methoxyphenyl)sulfanyl]benzo[b]thiophene-2-carboxylic acid (Example 23--218 mg, 0.49 mmol) in acetic acid (2 ml), and 2M hydrochloric acid (2 ml). The solution was heated to 100° C. for 1 hour. The solution was cooled and the solvents were evaporated under reduced pressure. The residue was dissolved in a hot mixture of aqueous sodium hydroxide (5 ml of 1M) and methanol (5 ml). After acidifying the solution with acetic acid, and cooling, the precipitate was collected by filtration to give the title compound as a colourless solid (95 mg).

Workup

  1. temperatureThe solution was cooled
  2. customthe solvents were evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in a hot mixture of aqueous sodium hydroxide (5 ml of 1M) and methanol (5 ml)
  4. temperaturecooling
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-cbb02c4d113d40268229afedee2d5b53
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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