Lithium Hydroxide → HCID 58074573, compound

HRID 1848360Notes

Reaction equation

HRID 1848360 reaction equation
C([O:3][C:4]([C:6]1([C:9]2[N:27]=[C:12]3[C:13]([O:25][CH3:26])=[CH:14][CH:15]=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=4)[N:11]3[N:10]=2)[CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-]>O1CCOCC1.O>[C:23]([C:19]1[CH:18]=[C:17]([C:16]2[N:11]3[N:10]=[C:9]([C:6]4([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]4)[N:27]=[C:12]3[C:13]([O:25][CH3:26])=[CH:14][CH:15]=2)[CH:22]=[CH:21][CH:20]=1)#[N:24]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58074667HCID 58074667, compound2×

Product 1

HCID 58074573HCID 58074573, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1-[5-(3-Cyano-phenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-cyclopropanecarboxylic acid ethyl ester (compound 188) (0.32 g, 0.88 mmol) was dissolved in 1,4-dioxan (10 mL) by heating. LiOH (0.06 g, 1.4 mmol) in H2O (2.5 mL) was added at RT. The suspension was stirred at RT overnight. The reaction mixture was concentrated in vacuo and H2O was added. The aqueous phase was washed with EtOAc and acidified with 4N HCl to pH 1. The aqueous phase was extracted with DCM (×2) and dried over MgSO4, filtered and concentrated in vacuo. This afforded the title compound as a solid.

Workup

  1. temperatureby heating
  2. concentrationThe reaction mixture was concentrated in vacuo and H2O
  3. additionwas added
  4. washThe aqueous phase was washed with EtOAc
  5. extractionThe aqueous phase was extracted with DCM (×2)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a48565ec991446cbb0a0bfb0ff871100
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

Loading…