3-(Trifluoromethoxy)benzene-1-sulfonyl chloride → N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)-3-(trifluoromethoxy)benzenesulfonamide

HRID 552440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552440
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:12][C:13](=[O:15])[NH:14][C:7]=12.[F:19][C:20]([F:33])([F:32])[O:21][C:22]1[CH:23]=[C:24]([S:28](Cl)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1>>[O:15]=[C:13]1[NH:12][C:8]2=[N:9][CH:10]=[CH:11][C:6]([O:5][C:4]3[CH:3]=[C:2]([NH:1][S:28]([C:24]4[CH:25]=[CH:26][CH:27]=[C:22]([O:21][C:20]([F:19])([F:32])[F:33])[CH:23]=4)(=[O:30])=[O:29])[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Komponenten

3

Edukt 2

HCID 27772183-(Trifluoromethoxy)benzene-1-sulfonyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Produkt 1

HCID 45140535N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)-3-(trifluoromethoxy)benzenesulfonamideAusbeute 84 %

Versuchsvorschrift

Method K was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-(trifluoromethoxy)benzenesulfonyl chloride to afford the title compound as an off-white solid (51 mg, 84%). 1H-NMR (δ, ppm, DMSO-d6): 6.20 (br s, 1H, HPy,5), 6.78 (s, 1H, Harom), 6.86 (d, 1H, Harom, J=7.5 Hz), 6.98 (d, 1H, Harom, J=7.4 Hz), 7.31-7.35 (m, 1H, Harom), 7.64-7.86 (m, 5H, Harom), 10.57 (s, 1H, NHSO2), 11.13 (s, 1H, NHPy3), 11.39 (s, 1H, NHPy2). 13C-NMR (δ, ppm, DMSO-d6): 106.18, 110.92, 113.71, 115.35, 116.48, 118.88, 121.88, 125.77, 125.83, 130.96, 131.93, 138.77, 141.03, 141.15, 144.12, 147.19, 148.23, 154.15, 154.99. HRMS (EI): m/z [M+H] calcd for C19H14F3N4O5S: 467.0637; found: 467.0644.

Quellen und Nachweise

ORD-Eintrag
ord-6c2afd344c3d4da98dcaf3e90e5858cd
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951819B2

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