Lithium Hydroxide → HCID 46830634, compound

HRID 1848338Notes

Reaction equation

HRID 1848338 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][C:20]([C:23]#[N:24])=[CH:19][CH:18]=4)[N:11]3[N:10]=2)[CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-]>O1CCOCC1>[C:23]([C:20]1[CH:19]=[CH:18][C:17]([C:16]2[N:11]3[N:10]=[C:9]([C:6]4([C:4]([OH:5])=[O:3])[CH2:8][CH2:7]4)[N:27]=[C:12]3[C:13]([O:25][CH3:26])=[CH:14][CH:15]=2)=[CH:22][CH:21]=1)#[N:24]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 46830633HCID 46830633, compound

Product 1

HCID 46830634HCID 46830634, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-[5-(4-Cyano-phenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-cyclopropanecarboxylic acid ethyl ester (0.39 g, 1.08 mmol) was suspended in 1,4-dioxan (10 mL) and aq. LiOH (68 mg, 1.6 mmol in 1.6 mL H2O) and stirred at it for 17 h. The mixture was concentrated in vacuo. The crude was suspended in H2O (3 mL) and 4N HCl (0.6 mL) was added. The aqueous phase was extracted with DCM (×3). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. This afforded the title compound as a slightly coloured solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. addition4N HCl (0.6 mL) was added
  3. extractionThe aqueous phase was extracted with DCM (×3)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-30c7648cb70442a9ae095ea3c3bb3dff
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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