Sodium Iodide → 6-(4-(3-acetylaminobenzoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

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Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 3-acetylaminobenzylchloride (200 mg), 6-(4-hydroxy-3-(trifluoromethyl)-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (350 mg), sodium iodide (16 mg) and potassium carbonate (300 mg) in acetonitrile (20 ml) was heated at 80° C. for 14 hours. After cooling to room temperature, water (30 ml) was added, the white precipitate collected by filtration was dissolved in DMSO (1 ml) and purified by HPLC to give 6-(4-(3-acetylaminobenzoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile. 1H NMR (DMSO) δ: 8.71 (s, 1H), 8.64 (s, 1H), 8.43 (m, 2H), 7.74 (s, 1H), 7.51 (m, 2H), 7.33 (t, 1H), 7.15 (d, 1H), 5.34 (s, 2H), 3.98 (s, 3H), 2.04 (s, 3H). MS m/z 466 (M+1).

Aufarbeitung

temperatureAfter cooling to room temperature
filtrationthe white precipitate collected by filtration
dissolutionwas dissolved in DMSO (1 ml)
custompurified by HPLC

Quellen und Nachweise

ORD-Eintrag: ord-4ece0bebc835413abffeb38e51eed17c
Quelldatensatz: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08026236B2

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