3-(Trifluoromethyl)phenylacetyl chloride → N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)-2-(3-trifluoromethylphenyl)acetamide

HRID 552426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552426
[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]([CH2:27][C:28](Cl)=[O:29])[CH:24]=[CH:25][CH:26]=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][C:28](=[O:29])[CH2:27][C:23]4[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([F:31])([F:19])[F:32])[CH:22]=4)[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Komponenten

3

Edukt 2

HCID 127516363-(Trifluoromethyl)phenylacetyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Produkt 1

HCID 45141109N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)-2-(3-trifluoromethylphenyl)acetamideAusbeute 33,3 %

Versuchsvorschrift

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]-pyridin-2(3H)-one and 2-(3-trifluoromethylphenyl)-acetyl chloride to afford the title compound (30 mg, 33.3%). 1H-NMR (δ, ppm, DMSO-d6): 3.77 (s, 2H, CH2), 6.43 (d, 1H, HPy,5, J=5.9 Hz), 6.83-6.86 (m, 1H, Harom), 7.34-7.64 (m, 7H, Harom), 7.67 (s, 1H, Harom), 7.78 (d, 1H, HPy,6, J=5.9 Hz), 10.39 (s, 1H, NHamide), 11.21 (s, 1H, NHPy7), 11.42 (s, 1H, NHPy9). LC-MS, tR=4.56 minutes, m/z: 429.05 (M+H)+, calculated for C21H16N4O3F3. HRMS (EI): m/z [M+H] calculated for C21H16N3O4F3: 429.1175; found: 429.1175.

Quellen und Nachweise

ORD-Eintrag
ord-f39ab1604ef649ba9a882573a70e69c2
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951819B2

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