3-chloro-5-(trifluoromethyl)benzoyl Chloride → N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)-3-trifluoromethyl-5-chloro-benzamide

HRID 552427

Reaktionsgleichung

Reaktionsgleichung von HRID 552427
[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:32])([F:31])[C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([Cl:30])[CH:29]=1)[C:24](Cl)=[O:25]>>[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][C:24](=[O:25])[C:23]4[CH:27]=[C:28]([Cl:30])[CH:29]=[C:21]([C:20]([F:32])([F:19])[F:31])[CH:22]=4)[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Komponenten

3

Edukt 2

HCID 38704343-chloro-5-(trifluoromethyl)benzoyl ChlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Produkt 1

HCID 45141111N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)-3-trifluoromethyl-5-chloro-benzamideAusbeute 29,8 %

Versuchsvorschrift

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]-pyridin-2(3H)-one and 3-trifluoromethyl-5-chlorobenzoyl chloride to afford the title compound (28 mg, 29.8%). 1H-NMR (δ, ppm, DMSO-d6): 6.50 (d, 1H, HPy,5, J=5.9 Hz), 6.94-6.96 (m, 1H, Harom), 7.45 (t, 1H, Harom-5, J=8.2 Hz), 7.59 (s, 1H, Harom-2), 7.63-7.65 (m, 1H, Harom), 7.81 (d, 1H, HPy,6, J=5.9 Hz), 8.12 (s, 1H, Harom′), 8.22 (s, 1H, Harom′), 8.30 (s, 1H, Harom′), 10.60 (s, 1H, NHamide), 11.20 (s, 1H, NHPy7), 11.39 (s, 1H, NHPy9). LC-MS, tR=5.07 minutes, m/z: 448.06 (M+H)+, calculated for C20H13N4O3F3Cl. HRMS (EI): m/z [M+H] calculated for C20H13N4O3F3Cl: 449.0628; found: 449.0619.

Quellen und Nachweise

ORD-Eintrag
ord-8b63bc81a2d848c4a9dff3c972c1b4b0
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951819B2

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