Lithium Hydroxide → HCID 58074618, compound

HRID 1848364Notes

Reaction equation

HRID 1848364 reaction equation
C([O:3][C:4]([C:6]1([C:9]2[N:20]=[C:12]3[C:13]([Br:19])=[CH:14][CH:15]=[C:16]([O:17][CH3:18])[N:11]3[N:10]=2)[CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-]>O1CCOCC1.O>[Br:19][C:13]1[C:12]2[N:11]([N:10]=[C:9]([C:6]3([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]3)[N:20]=2)[C:16]([O:17][CH3:18])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58074569HCID 58074569, compound

Product 1

HCID 58074618HCID 58074618, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1-(8-Bromo-5-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid ethyl ester (0.22 g, 0.64 mmol) was dissolved in 1,4-dioxan (15 mL). LiOH (0.085 g, 1.9 mmol) in H2O (3 mL) was added. The mixture was stirred at RT overnight. The solvent was evaporated. H2O (50 mL) was added and the aqueous phase was adjusted to pH 1 with 2 N HCl. The aqueous phase was extracted (×3) with EtOH/DCM 1/10. The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound as a solid.

Workup

  1. customThe solvent was evaporated
  2. additionH2O (50 mL) was added
  3. extractionThe aqueous phase was extracted (×3) with EtOH/DCM 1/10
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4462b80f2e9f409fa2d73637450c0bb0
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

Loading…