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

HRID 2189816Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[N:22]([CH2:26][C:27]([CH3:34])([CH3:33])[C:28]([O:30]CC)=[O:29])[N:21]=[CH:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[N:22]([CH2:26][C:27]([CH3:34])([CH3:33])[C:28]([OH:30])=[O:29])[N:21]=[CH:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]-2,2-dimethylpropanoate (D100) (85 mg, 176 mmol) in THF (2 ml) at room temperature was added NaOH (2N in H2O, 440 μl, 880 mmol) and the resulting mixture was stirred at 50° C. overnight. NaOH (2N in H2O, 440 μl, 880 mmol) and THF (2 ml) were added and the resulting mixture stirred at 80° C. for two nights then cooled to room temperature. Most of THF was removed in vacuo and the resulting aqueous phase was acidified to pH 3. The precipitate formed was filtered off and washed with H2O then dried at 60° C. under vacuum to give the title compound (73 mg, 91%) as a white solid. MS (ES): C23H23ClN4O4 requires 454; found (MH+) 455.

Workup

stirringthe resulting mixture stirred at 80° C. for two nights
temperaturethen cooled to room temperature
customMost of THF was removed in vacuo
customThe precipitate formed
filtrationwas filtered off
washwashed with H2O
customthen dried at 60° C. under vacuum

Sources & evidence

ORD record: ord-55b8a7e5f19b4a729a7fe0836494a88b
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324254B2

Reaction notes

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