Sodium Hydroxide → 3-[4-(5-{5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]-2,2-dimethylpropanoic acid

HRID 2189817Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[N:20][N:21]4[CH2:26][C:27]([CH3:34])([CH3:33])[C:28]([O:30]CC)=[O:29])[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[N:20][N:21]4[CH2:26][C:27]([CH3:34])([CH3:33])[C:28]([OH:30])=[O:29])[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 3-[4-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]-2,2-dimethylpropanoate (D105) (50 mg, 0.103 mmol) was dissolved in ethanol (10 ml). Sodium hydroxide (2N in H2O, 0.258 ml, 0.517 mmol) was added and the resulting mixture was stirred at 60° C. overnight then cooled to room temperature. Solvent was evaporated, then 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 (22 mg, 42%) as an off-white solid. MS (ES): C22H22ClN5O4 requires 455; found (MH+) 456.

Workup

temperaturethen cooled to room temperature
customSolvent was evaporated
additionthe residue was diluted with water
extractionthen extracted with EtOAc
washThe organic phase was washed with H2O
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8d478c47904c4dcc93f7f12fb90d08dd
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324254B2

Reaction notes

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