Lithium Hydroxide → 1-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid

HRID 1848340Notes

Reaction equation

HRID 1848340 reaction equation
C([O:3][C:4]([C:6]1([C:9]2[N:20]=[C:12]3[C:13]([O:18][CH3:19])=[CH:14][CH:15]=[C:16]([I:17])[N:11]3[N:10]=2)[CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-]>O1CCOCC1.O>[I:17][C:16]1[N:11]2[N:10]=[C:9]([C:6]3([C:4]([OH:5])=[O:3])[CH2:8][CH2:7]3)[N:20]=[C:12]2[C:13]([O:18][CH3:19])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 580746021-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid ethyl ester2×

Product 1

HCID 580745911-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid ethyl ester (compound 305) (0.06 g, 0.16 mmol) was suspended in 1,4-dioxan (1.4 mL) and LiOH (0.01 g, 0.23 mmol) in H2O (0.23 mL) was added. The suspension was stirred for 15 h. The mixture was concentrated in vacuo. H2O and 4N HCL (0.085 mL) was added. Brine was added and the aqueous phase was extracted with DCM (×3). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The title compound was obtained as a slightly coloured solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionH2O and 4N HCL (0.085 mL) was added
  3. additionBrine was added
  4. extractionthe aqueous phase was extracted with DCM (×3)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fed86daf4c324b81a28d5583512370ff
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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