Hydrogen Peroxide → 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylsulfonyl)ethyl]-1-naphthalenecarboxamide

HRID 1958871Notes

Reaction equation

[OH:1]O.[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2([C:34]([F:37])([F:36])[F:35])[O:15][N:14]=[C:13]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]([C:26]([NH:28][CH2:29][CH2:30][S:31]([CH3:33])=[O:32])=[O:27])=[CH:18][CH:17]=3)[CH2:12]2)[CH:7]=[C:8]([Cl:10])[CH:9]=1.[OH-].[Na+]>C(O)(=O)C.O>[Cl:10][C:8]1[CH:7]=[C:6]([C:11]2([C:34]([F:36])([F:35])[F:37])[O:15][N:14]=[C:13]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]([C:26]([NH:28][CH2:29][CH2:30][S:31]([CH3:33])(=[O:1])=[O:32])=[O:27])=[CH:18][CH:17]=3)[CH2:12]2)[CH:5]=[C:4]([Cl:3])[CH:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

H2O2 (0.056 mL, 30% in H2O) was added to a stirred solution of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylsulfinyl)ethyl]-1-naphthalenecarboxamide (i.e. the product of Example 2, 100 mg) in acetic acid (1.0 mL). The reaction mixture was stirred at 60° C. for 4 h, then cooled to room temperature, diluted with water, adjusted to pH 4 with 1.0 M aqueous NaOH solution, and extracted with chloroform. The organic extract was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to provide the title compound (100 mg), a compound of this invention, as a white solid. 1H NMR (CDCl3): δ 8.80 (d, 1H), 8.29 (d, 1H), 7.43-7.66 (m, 7H), 6.94 (br t, 1H), 4.24 (d, 1H), 4.04 (q, 2H), 3.40 (t, 2H), 3.01 (s, 3H).

Workup

temperaturecooled to room temperature
extractionextracted with chloroform
extractionThe organic extract
washwas washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-cdb869fbdd074ef88cfb05ae55d1d920
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410153B2

Reaction notes

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