4-Acetylbenzenesulphonamide → HCID 178419065, compound

HRID 10739Notes

Reaction equation

[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[C:10]1[C:11]([O:20][CH3:21])=[CH:12][C:13]([O:18][CH3:19])=[C:14]([CH:17]=1)[CH:15]=O.[C:22]([C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1)(=[O:24])[CH3:23]>>[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[C:10]1[C:11]([O:20][CH3:21])=[CH:12][C:13]([O:18][CH3:19])=[C:14](/[CH:15]=[CH:23]/[C:22]([C:25]2[CH:26]=[CH:27][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:29][CH:30]=2)=[O:24])[CH:17]=1

Participants

Reactant 2

HCID 740654-Acetylbenzenesulphonamide

HCID 178418995HCID 178418995, compound

Product 1

HCID 178419065HCID 178419065, compoundYield 26%

Procedure

The title compound was prepared by condensing 5-(3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethoxy-benzaldehyde (Ex-76A) with 4-acetyl-benzenesulfonamide (Ex-26A) in a similar manner as described in Ex-22. Yellow solid, 26% yield, mp>260° C. 1H-NMR (DMSO-d6) δ 8.73 (s, 1H), 8.31 (dd, J=1, 4 Hz, 1H), 8.26 (d, J=8 Hz, 2H), 8.05 (d, J=16 Hz, 1H), 7.89–7.97 (m, 3H), 7.82 (d, J=16 Hz, 1H), 7.17–7.21 (m, 1H), 6.89 (s, 1H), 4.09 (s, 3H), 4.03 (s, 3H). MS m/z=465([M+H]+, 65%), 256 (100%). HRMS (ES+) Calcd. for C23H20N4O5S: 465.1232. Found: 465.1240.

Sources & evidence

ORD record: ord-2d24683324d84ddc92f92a2159bf2ee5
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094801B2

Reaction notes

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