Sodium Hydroxide → 3-[5-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]-2,2-dimethylpropanoic acid

HRID 2189818Notes

Reaction equation

HRID 2189818 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[N:23]([CH2:27][C:28]([CH3:35])([CH3:34])[C:29]([O:31]CC)=[O:30])[N:22]=[CH:21]4)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Na+]>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[N:23]([CH2:27][C:28]([CH3:35])([CH3:34])[C:29]([OH:31])=[O:30])[N:22]=[CH:21]4)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59316793Ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]-2,2-dimethylpropanoate

Product 1

HCID 250604753-[5-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]-2,2-dimethylpropanoic acidYield 31.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]-2,2-dimethylpropanoate (D107) (50 mg, 0.106 mmol) was dissolved in Ethanol (10 ml). Sodium hydroxide (2N in H2O, 0.264 ml, 0.528 mmol) was added and the resulting mixture was stirred at room temperature for 2 h. Most of the solvent was removed in vacuo, and the residue was diluted with water. The aqueous phase was neutralised with a 2N HCl aqueous solution then extracted with EtOAc. The organic phase was washed with H2O, dried over MgSO4 and concentrated in vacuo to give the title compound (15 mg, 30%) as a light yellow solid. MS (ES): C23H24N5O4 requires 445; found (MH+) 446.

Workup

  1. customMost of the solvent was removed in vacuo
  2. additionthe residue was diluted with water
  3. extractionthen extracted with EtOAc
  4. washThe organic phase was washed with H2O
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c42423c667f43778241b27b4ea18e2a
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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