Hydrochloric Acid → HCID 66597510, compound

HRID 1627839Notes

Reaction equation

HRID 1627839 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([CH3:24])=[C:9]([CH2:19][C:20]([O:22]C)=[O:21])[C:10]=2[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[S:5][C:4]=1[CH3:25])[CH3:2].[O-2].[Li+].[Li+].Cl>O1CCOCC1.O>[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([CH3:24])=[C:9]([CH2:19][C:20]([OH:22])=[O:21])[C:10]=2[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[S:5][C:4]=1[CH3:25])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 166630Lithium oxideHCID 66597325HCID 66597325, compound

Product 1

HCID 66597510HCID 66597510, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 2-(3-ethyl-2,6-dimethyl-4-p-tolylthieno[2,3-b]pyridin-5-yl)acetate (0.045 g; 0.127 mmol) in dioxane (3 mL) and water (0.8 mL) was added a 1N lithium oxide solution (0.8 mL; 0.80 mmol). The reaction mixture was heated at 60° C. for 2 h. After cooling to room temperature, the reaction mixture was acidified with 1N HCl (pH˜2) and partially concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was crystallized from a mixture of ethyl acetate/heptane to afford 0.028 g (65%) of the title compound as a beige solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationpartially concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from a mixture of ethyl acetate/heptane

Sources & evidence

ORD record
ord-92341110ce074fc2acedb82660642cc2
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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