Ethyl 3-{[6-(acetylamino)pyridin-3-yl]ethynyl}-4-methylbenzoate → HCID 68899408, compound

HRID 1527892Notes

Reaction equation

HRID 1527892 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:16]([O:18]CC)=[O:17])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>C(O)C.[OH-].[Na+]>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:16]([OH:18])=[O:17])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 68898058Ethyl 3-{[6-(acetylamino)pyridin-3-yl]ethynyl}-4-methylbenzoate

Product 1

HCID 68899408HCID 68899408, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 3-{[6-(acetylamino)pyridin-3-yl]ethynyl}-4-methylbenzoate (0.68 mmol) in 5 ml of ethanol is cooled to 0° C. To this solution is dropped in 3 ml of 1M NaOH. The hydrolysis is stirred at this temperature for 2 h and r.t. for 3 h. The solvent (ethanol) is evaporated, and more water is added to dissolve the solid. The clear solution is washed with ether twice and then titrated with 2M HCl to pH 6. The precipitate is filtered, washed with water and ether, and dried to afford the product. The filtrate (pH 6) was extracted with DCM, dried, and evaporated to obtain additional amount of the hydrolyzed product.

Workup

  1. customThe solvent (ethanol) is evaporated
  2. additionmore water is added
  3. dissolutionto dissolve the solid
  4. washThe clear solution is washed with ether twice
  5. filtrationThe precipitate is filtered
  6. washwashed with water and ether
  7. customdried
  8. customto afford the product
  9. extractionThe filtrate (pH 6) was extracted with DCM
  10. customdried
  11. customevaporated
  12. customto obtain additional amount of the hydrolyzed product

Sources & evidence

ORD record
ord-83b299a9d82f45fa8483c55d978bc85e
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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