HCID 21879376, compound → N-2-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]ethyl-4-phenoxybenzenesulfonamide

HRID 724697Notes

Reaction equation

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

Participants

Conditions

Temperature: 170 °C

Procedure

N-2-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]ethyl-4-phenoxy-benzenesulfonamide (10.0 mg, 0.0184 mmol) was dissolved in trifluoroacetic acid (2 mL). The reaction was heated to 170° C. in the microwave and held at that temperature for 45 seconds. The reaction was chromatographed on a 21.2 mm Luna C18 column using a 20–80% acetonitrile in water gradient with 0.05% trifluoroacetic acid at 25 mL per minute over a 20 minute period. The major fraction was lyophilized to give a white powder (8 mg, 90%). 1H NMR (500 MHz, CD3OD): δ 7.76 (d, J=9.2 Hz, 2H), 7.42 (t, J=7.8 Hz, 2H), 7.37 (d, J=7.8 Hz, 2H), 7.24 (d, J=7.8 Hz, 2H), 7.21 (m, 1H), 7.07 (d, J=7.8 Hz, 2H), 7.03 (d, J=8.8 Hz, 2H), 4.94 (m, 1H), 4.39 (m, 1H), 3.35 (m, 2H), 3.24 (m, 2H), 2.85 (m, 2H); LCMS found for C23H22N2O6S2 (M+H)+: m/z 487.1.

Workup

customThe reaction was chromatographed on a 21.2 mm Luna C18 column
customover a 20 minute

Sources & evidence

ORD record: ord-9c378ddabeba4edba5bf8df7f4f94956
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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