Sodium Hydroxide → HCID 70981082, compound

HRID 1409357Notes

Reaction equation

HRID 1409357 reaction equation
[CH3:1][N:2]([CH3:20])[C:3](=[O:19])[NH:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[C:12]([C:14]([O:16]CC)=[O:15])[N:13]=2)[CH:10]=1.[OH-].[Na+]>C(O)C>[CH3:1][N:2]([CH3:20])[C:3](=[O:19])[NH:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70980938HCID 70980938, compound

Product 1

HCID 70981082HCID 70981082, compoundYield 112.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 6-(3,3-dimethylureido)imidazo[1,2-a]pyridine-2-carboxylate (0.239 mmol, 0.066 g) was dissolved in ethanol (5 ml). The solution was cooled to 0° C. and NaOH 2 M solution (0.478 mmol, 0.239 ml) was added. The resulting mixture was stirred at 0° C. Ethanol was evaporated and water was added. The pH of the water phase was adjusted to ˜4 with HCl. The mixture was extracted with EtOAc and the organic phase was dried, filtered and evaporated. The residue was triturated with MeOH/DCM 1/9. The filtered precipitate was dried under vacuum. 0.067 g of the title compound was obtained. LC-MS: [M−1]=247.24.

Workup

  1. customEthanol was evaporated
  2. additionwater was added
  3. extractionThe mixture was extracted with EtOAc
  4. customthe organic phase was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with MeOH/DCM 1/9
  8. customThe filtered precipitate was dried under vacuum

Sources & evidence

ORD record
ord-2888960196a54bc086649a89d3b27059
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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