4-Acetylbenzenesulphonamide → 2-{5-Methoxy-2-[3-oxo-3-(4-aminosulfonyl-phenyl)-E-propenyl]-4-thiophen-2-yl-phenoxy}-2-methyl-propionic acid

HRID 10705

Reaction equation

HRID 10705 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH:14]([C:16]1[CH:28]=[C:27]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)[C:26]([O:34][CH3:35])=[CH:25][C:17]=1[O:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])=O>>[CH3:35][O:34][C:26]1[C:27]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[CH:28][C:16](/[CH:14]=[CH:2]/[C:1](=[O:3])[C:4]2[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=2)=[C:17]([CH:25]=1)[O:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21]

Participants

3

Reactant 2

HCID 740654-AcetylbenzenesulphonamideHCID 219810292-(2-Formyl-5-methoxy-4-thiophen-2-yl-phenoxy)-2-methyl-propionic acid

Product 1

HCID 100975432-{5-Methoxy-2-[3-oxo-3-(4-aminosulfonyl-phenyl)-E-propenyl]-4-thiophen-2-yl-phenoxy}-2-methyl-propionic acidYield 85%

Procedure

The title compound was prepared by condensing 4-acetyl-benzenesulfonamide (Ex-26A) and 2-(2-formyl-5-methoxy-4-thiophen-2-yl-phenoxy)-2-methyl-propionic acid (Ex-59B) in a similar manner as described in Ex-22. Yellow solid, mp 164–165° C., 85% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.21–8.28 (m, 3H), 7.96–8.12 (m, 4H), 7.67 (d, 1H, J=3.0 Hz), 7.56 (brs, 3.0H), 7.14 (dd, 1H, J=5.7, 3.0 Hz), 6.57 (s, 1H), 3.88 (s, 3H), 1.66 (s, 6H). MS (ESI) m/z=502 ([M+H]+, 100%). Anal. Calcd. for C24H23NO7S2: C, 57.47; H, 4.62; N, 2.79; S, 12.79. Found: C, 57.70; H, 4.74; N, 2.85; S, 12.51.

Sources & evidence

ORD record
ord-e307b28fe0b34d59bb0d8a3d4186d652
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Linked notes

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