Potassium Hydroxide → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-carbamoyl-3-hydroxy-3-(2-naphthyl)oxindole

HRID 1369072Notes

Reaction equation

[CH2:1]([N:3]([CH2:33][CH3:34])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[C:8]([OH:31])([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[C:7]1=[O:32])[CH3:2].[OH-:35].[K+]>C(O)(C)(C)C>[CH2:33]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:18])([F:20])[F:19])[CH:11]=[C:12]([C:15](=[O:35])[NH2:16])[CH:13]=2)[C:8]([OH:31])([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[C:7]1=[O:32])[CH3:34]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-cyano-3-hydroxy-3-(2-naphthyl)oxindole of Example 55 (185 mg, 0.396 mmol) in t-butanol (8 mL) was added powdered KOH (ca. 1 g) at 50° C. The mixture was stirred for 1 h at 50° C. and passed through a celite pad. The celite was washed with THF and the filtrate was concentrated. The residue was dispersed between water and ethyl acetate and the organic layer was separated. The organic layer was dried over MgSO4 and concentrated to give the title compound (198 mg, quant.). The hydrochloride of the title compound was obtained by treating with 4 N HCl in dioxane followed by concentration to dryness.

Workup

washThe celite was washed with THF
concentrationthe filtrate was concentrated
additionThe residue was dispersed between water and ethyl acetate
customthe organic layer was separated
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-34f43ebae4f749628982cb84de309431
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06576656B1

Reaction notes

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