Sodium Hydroxide → HCID 70980721, compound

HRID 1409360Notes

Reaction equation

HRID 1409360 reaction equation
[CH3:1][S:2]([N:5]([C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:16]=[C:17]([C:19]([O:21]CC)=[O:20])[N:18]=2)[CH:15]=1)S(C)(=O)=O)(=[O:4])=[O:3].[OH-].[Na+]>C(O)C>[CH3:1][S:2]([NH:5][C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:16]=[C:17]([C:19]([OH:21])=[O:20])[N:18]=2)[CH:15]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131732205HCID 131732205, compound

Product 1

HCID 70980721HCID 70980721, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 6-(N-(methylsulfonyl)methylsulfonamido)imidazo[1,2-a]pyridine-2-carboxylate (0.412 mmol, 0.149 g) was dissolved in ethanol (10 ml) and cooled to 0° C. with an ice bath. NaOH 2 M solution (0.825 mmol, 0.412 ml) was added and stirred at 0° C. for 3.5 h after which the temperature was allowed to warm to RT. The stirring continued overnight. The temperature was raised to 50° C. and stirred for 5 h. The mixture was again stirred at RT overnight. Ethanol was evaporated and water was added. The pH was adjusted to 4 with 1 M HCl after which the product started to precipitate. The precipitate was removed by filtration and dried under vacuum. 0.057 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 3.05 (s, 3H), 7.22-7.29 (m, 1H), 7.60-7.66 (m, 1H), 8.49-8.53 (m, 1H), 8.55 (s, 1H), 9.81 (s, 1H).

Workup

  1. temperatureto warm to RT
  2. customThe stirring continued overnight
  3. temperatureThe temperature was raised to 50° C.
  4. stirringstirred for 5 h
  5. stirringThe mixture was again stirred at RT overnight
  6. customEthanol was evaporated
  7. additionwater was added
  8. customto precipitate
  9. customThe precipitate was removed by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-653d03f1c7694af4b87901bbcaee959b
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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